Herbicidal 5-pyrimidinecarbonitriles

ABSTRACT

5-Pyrimidinecarbonitriles, having amino substituents in the 2 and 6 positions and an alkoxy substituent in the 4 position, exhibit herbicidal activity. The preparation of novel active compounds and intermediates in this class is described; herbicidal compositions containing the active compounds are illustrated; and methods for utilizing the herbicidal compositions to control plant growth are disclosed.

REFERENCE TO PRIOR APPLICATION

This is a Continuation-In-Part of Application Ser. No. 718,224, filedAug. 27, 1976, now abandoned.

BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention pertains to the general field of herbicides, to novelherbicidal compounds and intermediates thereto, as well as tocompositions containing the active compounds, and to new methods for thecontrol of undesired plant growth by preemergence or postemergenceapplication of the novel active compounds and compositions.

2. Description of the Prior Art

It has long been man's desire to promote the growth of certain plantspecies, those species which serve as food for man or for his animals,species which protect him from the elements, such as trees andshrubbery, and species which he finds aesthetically attractive, such asflowers. Centuries ago man learned to promote the growth of plants byapplying fertilizer to them. Great commercial enterprises have beenbuilt upon processes for producing ammonia, urea, phosphates, potash,and other materials incorporated into fertilizer compositions. The valuein the use of fertilizer for promoting plant growth is well known.

Man has probably always realized that certain foreign plant species,weeds, compete with his crops for the available sunlight, air, andnutrients in the soil. However, it is only recently, with theexponential growth in the world's population and the resultant demandsplaced upon the world's food supply, that man has developed thetechnical ability to selectively retard or prevent the growth ofundesired plant species growing with his crops. One of the firstherbicides was 2,4-dichlorophenoxyacetic acid (2,4-D), which becameavailable in 1944 for the control of broad-leaved weeds. Since then, anumber of other classes of herbicides have appeared, some of which aremore selective than 2,4-D, give control at much lower rates ofapplication, are less toxic to mammals, longer lasting, easier to use,cheaper, and do not leave residues harmful to the environment. All ofthese characteristics are desirable features for a herbicide to possess.

Heterocyclic organic compounds are among the newer classes ofherbicides. For example, the six-member s-triazine ring system is thecentral structural feature in a number of commercial herbicides,including 2-t-butylamino-4-ethylamino-6-methoxy-s-triazine [Martin andWorthing, "Pesticide Manual," 4th Ed., British Crop Protection Council,Worcester, England, 1974, p. 477],2-sec-butylamino-4-ethylamino-6-methoxy-s-triazine [ibid., p. 449],2-chloro-4-cyclopropylamino-6-isopropylamino-s-triazine [ibid., p. 146],2-chloro-4-ethylamino-6-isopropylamino-s-triazine [ibid., p. 23], and2-chloro-4-(1-cyano-1-methylethylamino)-6-ethylamino-s-triazine [ibid.,p. 137].

The six member 1,3-diazine (pyrimidine) ring system is less common amongthe known herbicides, but some 4,6-disubstituted and2,4,6-trisubstituted 5-nitropyrimidines display herbicidal activity[Ger. Offen. 2,520,381] as do certain2,6-diamino-5-pyrimidinecarboxamides [U.S. Pat. No. 3,845,055].

It has now been discovered that 5-pyrimidinecarbonitriles, having aminosubstituents in the 2 and 6 positions and an alkoxy substituent in the 4position, are extremely effective herbicides, which control the growthof a range of grassy and broad-leaved weeds while not affectingdesirable crops such as corn and cotton growing therewith. One advantageof the 2,4,6-trisubstituted 5-pyrimidinecarbonitriles of this inventionis that many of them are effective at very low rates of application.

SUMMARY OF THE INVENTION

The novel active 5-pyrimidinecarbonitriles of this invention and thenovel compounds useful as intermediates thereto are representedcollectively by the following structural formula: ##STR1## wherein R² isa radical selected from amino, lower alkylamino, lower cycloalkylamino,di(lower alkyl)amino, [alpha-cyano(lower alkyl)]amino, and halogen; R⁴is a radical selected from lower alkoxy, and halogen; and R⁶ is aradical selected from amino, lower alkylamino, lower cycloalkylamino,di(lower alkyl)amino, and halogen; with the proviso that no more thantwo of R², R⁴ and R⁶ are halogen; and provided further that neither R²nor R⁶ is tert-butylamino; and when R² is isopropylamino, R⁶ is otherthan n-butylamino; and when R² is methylethylamino, R⁶ is other thanisopropylamino; and when R² is diethylamino, R⁶ is other than amino. Indefining R², R⁴, and R⁶, the term "lower" means 1-7 carbon atoms,preferably 1-4 carbon atoms.

These novel intermediates and the novel active 5-pyrimidinecarbonitrilesprepared therefrom can be obtained conveniently from a2,4,6-trihalo-5-pyrimidinecarbonitrile.2,4,6-Trichloro-5-pyrimidinecarbonitrile is available from barbituricacid and urea via 2,4,6-trihydroxy-5-pyrimidinecarboxamide [Scarboroughand Gould, J. Org. Chem., 26, 3720 (1961); U.S. Pat. No. 3,097,910].Alpha-aminonitriles are employed in preparing 5-pyrimidinecarbonitrilescontaining an [alphacyano(lower-alkyl)]amino group in the R² position.Alpha-aminonitriles may be prepared by the Strecker synthesis[Freifelder and Hasbrouck, J. Amer. Chem. Soc., 82, 696 (1960)].

The novel intermediates of this invention contain at least one, but nomore than two, halogen atoms, preferably chlorine. They are obtained bythe displacement of one or two of the halogen atoms of a2,4,6-trihalo-5-pyrimidinecarbonitrile. Among the former, especiallyuseful intermediates comprise4,6-dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile,4,6-dichloro-2-isopropylamino-5-pyrimidinecarbonitrile and4,6-dichloro-2-(1-methylpropylamino)-5-pyrimidinecarbonitrile; whereasamong the latter,4-chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrile,4-chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile,4-chloro-2-(1-cyano-1-methylethylamino)-6-cyclopropylamino-5-pyrimidinecarbonitrile,4-chloro-6-cyclopropylamino-2-isopropylamino-5-pyrimidinecarbonitrile,and4-chloro-6-cyclopropylamino-2-(1-methylpropylamino)-5-pyrimidinecarbonitrileare especially useful.

In the novel active 5-pyrimidinecarbonitriles of this invention allthree of the halogen atoms of the 2,4,6-trihalo-5-pyrimidinecarbonitrileare displaced, so that R² is a radical selected from amino, loweralkylamino, lower cycloalkylamino, di(lower alkyl)amino, and[alpha-cyano(lower alkyl)]amino; R⁴ is a lower alkoxy radical; and R⁶ isa radical selected from amino, lower alkylamino, lower cycloalkylamino,and di(lower alkyl)amino; with the proviso that neither R² nor R⁶ istert-butylamino; and provided further that when R² is isopropylamino, R⁶is other than n-butylamino; and when R² is methylethylamino, R⁶ is otherthan isopropylamino; and when R² is diethylamino, R⁶ is other thanamino.

Preferred active compounds result when R² is selected from loweralkylamino (except tert-butylamino) and [alpha-cyano-(loweralkyl)]amino; and R⁶ is selected from lower alkylamino (excepttert-butylamino) and lower cycloalkylamino.

Especially preferred active compounds result if R² is selected fromethylamino, isopropylamino, 1-methylpropylamino, 2-methylpropylamino,and 1-cyano-1-methylethylamino; R⁴ is methoxy or ethoxy; and R⁶ isselected from ethylamino, isopropylamino and cyclopropylamino.

The herbicidal compositions of this invention each contain anherbicidally effective amount of at least one active5-pyrimidinecarbonitrile. The herbicidal compositions may take the formof granules, wettable powders, emulsifiable concentrates, solutions, orother known forms, depending on the mode of application.

The method of controlling the growth of undesired plant species withinthe contemplation of this invention involves applying to the area to beprotected an herbicidal composition containing an herbicidally effectiveamount of at least one active 5-pyrimidinecarbonitrile. A variety ofmethods of application may be utilized and are well known in the art.These include preemergence application of an herbicidal composition tothe soil before planting seeds therein or to both the soil and the seedsafter the seeds are sown, as well as postemergence application togrowing plants.

The synthesis of the herbicidal 5-pyrimidinecarbonitriles from2,4,6-trichloro-5-pyrimidinecarbonitrile is described by the followingchemical equations.

DETAILED DESCRIPTION OF THE INVENTION

Syntheses of the active 5-pyrimidinecarbonitriles and intermediatesthereto are illustrated in the following Examples, wherein alltemperatures are in degrees centigrade and pressures are in mm ofmercury. ##STR2##

EXAMPLE I 2,4,6-Trihydroxy-5-pyrimidinecarboxamide

A mixture of 128 grams of barbituric acid and 120 grams of urea in 200ml of 1-methyl-2-pyrrolidone was heated at 145° for 15 minutes. Hotwater was then added to the reaction mixture; a white solid precipitatedand was collected by filtration. The precipitate was washed with hotdimethylformamide and dried to give 165 grams of2,4,6-trihydroxy-5-pyrimidinecarboxamide; mp, >270°. The mass spectrumof the product was consistent with the assigned structure.

EXAMPLE II 2,4,6-Trichloro-5-pyrimidinecarbonitrile

A stirred mixture of 40 grams (24 ml) of phosphorus oxychloride and 9grams of 2,4,6-trihydroxy-5-pyrimidinecarboxamide was refluxed for 1hour. An additional 12 ml of phosphorus oxychloride was then added, andthe mixture was refluxed for an additional 3 hours. The excessphosphorus oxychloride was removed by distillation, and the residue waspoured into a mixture of ice and water. The aqueous mixture wasextracted with chloroform. The extract was dried with magnesium sulfateand filtered. The filtrate was evaporated under reduced pressure to aresidue. The residue was sublimed to give 2 grams of2,4,6-trichloro-5-pyrimidinecarbonitrile; mp, 117°-119°. The massspectrum of the product was consistent with the assigned structure.

EXAMPLE III 2-Amino-2-methylpropionitrile

To a stirred solution of 54 grams of sodium cyanide in 250 ml of waterat room temperature was added 73 grams of ammonium sulfate. The reactionmixture was cooled to 10°-15°, and 58 grams of acetone was addeddropwise. Upon complete addition, the stirred reaction mixture wasallowed to stand at room temperature for 60 hours. The organic layer wasseparated, and the aqueous layer was extracted with diethyl ether. Theextract was combined with the organic layer, and the combination wasdried over magnesium sulfate. The mixture was filtered, and the filtratewas evaporated under reduced pressure at room temperature to a residue.The residue was distilled under reduced pressure to give 24 grams of2-amino-2-methylpropionitrile; bp, 74°-82°/70 mm. The NMR spectrum ofthe product was consistent with the assigned structure.

EXAMPLE IV4,6-Dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile

A stirred solution of 6.3 grams of2,4,6-trichloro-5-pyrimidinecarbonitrile in 25 ml of acetone was cooledto -10°, and 2.5 grams of 2-amino-2-methylpropionitrile was added. Withthe reaction mixture at -10°, a solution of 1.3 grams of sodiumhydroxide in 3.5 ml of water was added dropwise. Upon complete addition,the reaction mixture was stirred at -10° for 30 minutes. The acetone wasremoved under reduced pressure; the residue was extracted with diethylether, and the extract was separated and dried over magnesium sulfate.The extract was filtered, and the filtrate was evaporated under reducedpressure, yielding a residue. The residue was recrystallized frommethylcyclohexane to give 3.1 grams of4,6-dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile;mp, 154°-158°.

Analysis: Calculated for C₉ H₇ Cl₂ N₅ : C,42.21; H,2.73; N,27.34; Found:C,42.26; H,2.92; N,27.35.

EXAMPLE V 4,6-Dichloro-2-ethylamino-5-pyrimidinecarbonitrile

A stirred solution of 12.9 grams of2,4,6-trichloro-5-pyrimidinecarbonitrile in 150 ml of acetone was cooledto -10°, and 7.7 grams of an aqueous 70% ethylamine solution was addeddropwise during 2 hours. The temperature of the reaction mixture wasmaintained at -10° throughout the addition. Following complete addition,the reaction mixture was allowed to warm to room temperature, where itstood for 16 hours. Then most of the acetone was removed by evaporationunder reduced pressure. The residue was extracted with a mixture ofwater and diethyl ether. The ether layer was separated and dried overmagnesium sulfate. The dried ether layer was filtered, and the ether wasremoved under reduced pressure. The residue was recrystallized from amixture of methylcyclohexane and benzene, then from carbontetrachloride, to give 4.2 grams of 4,6-dichloro-2-ethylamino-5-pyrimidinecarbonitrile; mp, 145°-150°.

Analysis: Calculated for C₇ H₆ Cl₂ H₄ : C,38.74; H,2.78; N,25.80; Found:C,38.47; H,2.97; N,25.90.

EXAMPLE VI 4,6-Dichloro-2-isopropylamino-5-pyrimidinecarbonitrile

A stirred solution of 4.2 grams of2,4,6-trichloro-5-pyrimidinecarbonitrile in 100 ml of diethyl ether wascooled to between -5° and -10°, and a solution of 2.4 grams ofisopropylamine in 100 ml of diethyl ether was added dropwise. Uponcomplete addition, water was added to the reaction mixture, and theether layer was separated. The ethereal layer was dried over magnesiumsulfate and filtered. The filtrate was evaporated to dryness underreduced pressure. The residue was recrystallized from methylcyclohexaneto give 2.4 grams of4,6-dichloro-2-isopropylamino-5-pyrimidinecarbonitrile; mp, 179°-181°.

Analysis: Calculated for C₈ H₈ Cl₂ N₄ : C,41.57; H,3.47; N,24.23; Found:C,41.33; H,3.35; N,23.97.

EXAMPLE VII4,6-Dichloro-2-(1-cyano-1-methylpropylamino)-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example IV, substituting2-amino-2-methylbutyronitrile for 2-amino-2-methylpropionitrile. The2-amino-2-methylbutyronitrile was prepared in the manner of Example III.The reaction product was recrystallized from carbon tetrachloride togive4,6-dichloro-2-(1-cyano-1-methylpropylamino)-5-pyrimidinecarbonitrile;mp, 130°-147°.

EXAMPLE VIII 4,6-Dichloro-2-diethylamino-5-pyrimidinecarbonitrile

A stirred solution of 6.3 grams of2,4,6-trichloro-5-pyrimidinecarbonitrile in 150 ml of diethyl ether wascooled to -10°, and a solution of 4.4 grams of diethylamine in 75 ml ofdiethyl ether was added dropwise. Upon complete addition, the reactionmixture was stirred at -10° for 1 hour. Water was added to the reactionmixture. The diethyl ether layer was separated and dried over magnesiumsulfate. The mixture was filtered, and the filtrate was evaporated underreduced pressure to a residue. The residue was recrystallized frommethylcyclohexane to give 3.8 grams of4,6-dichloro-2-diethylamino-5-pyrimidinecarbonitrile; mp, 125°-126°.

Analysis: Calculated for C₉ H₁₀ Cl₂ N₄ : C,44.10; H,4.07; N,22.85;Found: C,44.13; H,4.28; N,23.14.

EXAMPLE IX 4,6-Dichloro-2-methylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example V, substitutingaqueous 40% methylamine for aqueous 70% ethylamine. The reaction productwas recrystallized from actone to give4,6-dichloro-2-methylamino-5-pyrimidinecarbonitrile; mp, 222°-225°.

Analysis: Calculated for C₆ H₄ N₄ C₁₂ : C,35.50; H,1.97; N,27.60; Found:C,35.85; H,2.12; N,27.90.

EXAMPLE X 4-Chloro-2,6-bis(methylamino)-5-pyrimidinecarbonitrile

The crude reaction product of Example IX, approximately 19%4,6-dichloro-2-methylamino-5-pyrimidinecarbonitrile and 72%2,4-dichloro-6-methylamino-5-pyrimidinecarbonitrile, was treated withaqueous 40% methylamine in the manner of Example V, to give4-chloro-2,6-bis(methylamino)-5-pyrimidinecarbonitrile; mp, 281°-284° C.

Analysis: Calculated for C₇ H₈ ClN₅ : C,42.60; H,4.05; N,35.50; Found:C,42.80; H,4.24; N,35.44.

EXAMPLE XI4-Chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile

To a stirred solution of 5.1 grams of4,6-dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile in100 ml of acetone, 2.3 grams of isopropylamine was added dropwise. Thereaction mixture was then stirred at room temperature for 16 hours. Theacetone was removed under reduced pressure, and the reaction mixture wasextracted with a mixture of diethyl ether and water. The organic layerwas separated and dried over magnesium sulfate. The solution wasfiltered, and the filtrate was evaporated under reduced pressure,yielding a residue. The residue was recrystallized frommethylcyclohexane to give 2.7 grams of4-chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile;mp, 144°-147°.

Analysis: Calculated for C₁₂ H₁₅ ClN₆ : C,51.70; H,5.42; N,30.14; Found:C,51.05; H,5.20; N,29.85.

EXAMPLE XII4-Chloro-2-(1-cyano-1-methylpropylamino)-6-isopropylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example X, substituting4,6-dichloro-2-(1-cyano-1-methylpropylamino)-5-pyrimidinecarbonitrilefor4,6-dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile, togive4-chloro-2-(1-cyano-1-methylpropylamino)-6-isopropylamino-5-pyrimidinecarbonitrile;mp, 161°-166°.

Analysis: Calculated for C₁₃ H₁₇ ClN₆ : C,53.33; H,5.85; N,28.70; Found:C,53.22; H,5.78; N,28.75.

EXAMPLE XIII4-Chloro-6-ethylamino-2-isopropylamino-5-pyrimidinecarbonitrile

A stirred solution of 3.5 grams of4,6-dichloro-2-isopropylamino-5-pyrimidinecarbonitrile in 100 ml ofacetone was cooled to between 0° and -5°; a solution of 2.1 grams ofaqueous 70% ethylamine in 25 ml of acetone was added dropwise. Uponcomplete addition, the reaction mixture was warmed to room temperatureand stirred for 18 hours. The acetone was removed under reducedpressure, and the residue was extracted with a mixture of diethyl etherand water. The organic layer was separated and dried over magnesiumsulfate. The mixture was filtered, and the filtrate was evaporated todryness under reduced pressure. The residue was recrystallized frommethylcyclohexane to give 3.1 grams of4-chloro-6-ethylamino-2-isopropylamino-5-pyrimidinecarbonitrile; mp,144°-146°.

Analysis: Calculated for C₉ H₁₂ ClN₅ : C,47.90; H,5.35; N,31.03; Found:C,47.70; H,5.40; N,31.15.

EXAMPLE XIV 4-Chloro-2,6-bis(ethylamino)-5-pyrimidinecarbonitrile

To a stirred solution of 6.3 grams of2,4,6-trichloro-5-pyrimidinecarbonitrile in 75 ml of acetone was addeddropwise 7.7 grams of an aqueous solution of 70% ethylamine. Uponcomplete addition, the reaction mixture was stirred at room temperaturefor 60 hours. The acetone was removed by evaporation under reducedpressure. The residue was extracted with a mixture of diethyl ether andwater, and 2.9 grams of insoluble4-chloro-2,6-bis(ethylamino)-5-pyrimidinecarbonitrile, mp, 190°-191°,remained.

Analysis: Calculated for C₉ H₁₂ ClN₅ : C,47.90; H,5.35; N,31.03; Found:C,47.70; H,5.40; N,31.15.

EXAMPLE XV 4-Chloro-2,6-bis(diethylamino)-5-pyrimidinecarbonitrile

To a stirred solution of 6.3 grams of2,4,6-trichloro-5-pyrimidinecarbonitrile in 150 ml of diethyl ether at10° was added dropwise 8.8 grams of diethylamine in 150 ml of diethylether. Upon complete addition, the reaction mixture was allowed to warmto room temperature, where it was stirred for 16 hours. The reactionmixture was heated under reflux for 1 hour, then cooled to roomtemperature. The reaction mixture was washed with water, and the diethylether layer was separated. The aqueous layer was washed with diethylether. The ether layers were combined and dried over magnesium sulfate.The mixture was filtered, and the filtrate was evaporated under reducedpressure to a residue. The residue was recrystallized from petroleumether to give crude4-chloro-2,6-bis(diethylamino)-5-pyrimidinecarbonitrile. This crudematerial was dissolved in diethyl ether, and 4.4 grams of diethylaminewas added.

The reaction mixture stood at room temperature for 16 hours. Thereaction mixture was washed with water, and the diethyl ether layer wasseparated. The ether layer was dried over magnesium sulfate andfiltered. The filtrate was evaporated under reduced pressure to aresidue. The residue was recrystallized from petroleum ether to give 3.2grams of 4-chloro-2,6-bis(diethylamino)-5-pyrimidinecarbonitrile; mp,40°-42°.

Analysis: Calculated for C₁₃ H₂₀ ClN₅ : C,55.41; H,7.15; N,24.85; Found:C,55.41; H,7.39; N,25.30.

EXAMPLE XVI4-Chloro-6-diethylamino-2-isopropylamino-5-pyrimidinecarbonitrile

To a stirred solution of 4.3 grams of4,6-dichloro-2-isopropylamino-5-pyrimidinecarbonitrile in 125 ml ofdiethyl ether was added dropwise 2.6 grams of diethylamine. Uponcomplete addition, the reaction mixture was stirred at room temperaturefor 1.5 hours. The reaction mixture was washed with water. The diethylether layer was separated and dried over magnesium sulfate. The mixturewas filtered, and the filtrate was evaporated under reduced pressure toa residue. The residue was recrystallized from methylcyclohexane to give2.5 grams of4-chloro-6-diethylamino-2-isopropylamino-5-pyrimidinecarbonitrile; mp,74°-76°.

Analysis: Calculated for C₁₂ H₁₈ ClN₅ : C,53.83; H,6.74; N,26.15; Found:C,53.42; H,6.54; N,25.85.

EXAMPLE XVII4-Chloro-2-ethylamino-6-isopropylamino-5-pyrimidinecarbonitrile

To a stirred solution of 6.5 grams of4,6-dichloro-2-ethylamino-5-pyrimidinecarbonitrile in 100 ml of acetonewas added dropwise 7.4 grams of isopropylamine in 30 ml of acetone. Uponcomplete addition, the reaction mixture was stirred at room temperaturefor 16 hours. The acetone was removed by evaporation under reducedpressure, and the solid residue was washed with water. The resultantsolid was collected by filtration to give 6.8 grams of4-chloro-2-ethylamino-6-isopropylamino-5-pyrimidinecarbonitrile; mp160°-165°. Recrystallization from a mixture of benzene andmethylcyclohexane gave purified product; mp, 163°-165°.

Analysis: Calculated for C₁₀ H₁₄ ClN₅ : C,50.10; H,5.88; N,29.21; Found:C,49.96; H,6.15; N,29.06.

EXAMPLE XVIII4-Chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrile

A stirred solution of 5.1 grams of4,6-dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile in50 ml of acetone was cooled to 0° to -5°, and 2.8 grams of an aqueoussolution of 70% ethylamine in 40 ml of acetone was added dropwise. Thetemperature of the reaction mixture was maintained at 0° to -5°throughout the addition, then during 2 hours following completeaddition. The reaction mixture was warmed to room temperature where itwas stirred for 1 hour. Water was added to the reaction mixture, whichcaused precipitation of a solid. The solid was collected by filtrationand recrystallized from a mixture of benzene and methylcyclohexane togive 3.3 grams of4-chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrile;mp, 157°-160°.

Analysis: Calculated for C₁₁ H₁₃ ClN₆ : C,50.59; H,5.18; N,31.55; Found:C,50.61; H,4.88; N,31.80.

EXAMPLE XIX4-Chloro-6-isopropylamino-2-methylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XVII, substituting4,6-dichloro-2-methylamino-5-pyrimidinecarbonitrile for4,6-dichloro-2-ethylamino-5-pyrimidinecarbonitrile. The reaction productwas recrystallized from benzene to give4-chloro-6-isopropylamino-2-methylamino-5-pyrimidinecarbonitrile; mp,218°-220°.

Analysis: Calculated for C₉ H₁₂ ClN₅ : C,47.90; H,5.36; N,31.03; Found:C,47.47; H,5.33; N,31.94.

EXAMPLE XX4-Chloro-2-isopropylamino-6-methylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XVII, substituting4,6-dichloro-2-isopropylamino-5-pyrimidinecarbonitrile and aqueous 40%methylamine for 4,6-dichloro-2-ethylamino-5-pyrimidinecarbonitrile andisopropylamine. The reaction product was recrystallized frommethylcyclohexane to give4-chloro-2-isopropylamino-6-methylamino-5-pyrimidinecarbonitrile; mp,170°-173°.

Analysis: Calculated for C₉ H₁₂ ClN₅ : C,47.90; H,5.36; N,31.03; Found:C,48.12; H,5.59; N,31.10.

EXAMPLE XXI4-Chloro-6-diethylamino-2-ethylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XVII, substitutingdiethylamine for isopropylamine. The product was4-chloro-6-diethylamino-2-ethylamino-5-pyrimidinecarbonitrile; mp,144°-146°.

Analysis: Calculated for C₁₁ H₁₅ ClN₅ : C,52.28; H,5.98; N,27.71; Found:C,52.05; H,6.09; N,27.93.

EXAMPLE XXII4-Chloro-2-(1-cyano-1-methylethylamino)-6-(1-methylbutylamino)-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example X, substituting2-aminopentane for isopropylamine. The reaction product wasrecrystallized from a mixture of benzene and methylcyclohexane to give4-chloro-2-(1-cyano-1-methylethylamino)-6-(1-methylbutylamino)-5-pyrimidinecarbonitrile;mp, 133°-135°.

Analysis: Calculated for C₁₄ H₁₉ C,N₆ : C,54.80; H,6.24; N,27.39; Found:C,54.91; H,6.41; N,27.59.

EXAMPLE XXIII4-Chloro-2-(1-cyano-1-methylethylamino)-6-(1-isopropyl-2-methylpropylamino)-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example X, substituting1-isopropyl-2-methylpropylamine for isopropylamine. The reaction productwas recrystallized from a mixture of benzene and methylcyclohexane togive4-chloro-2-(1-cyano-1-methylethylamino)-6-(1-isopropyl-2-methylpropylamino)-5-pyrimidinecarbonitrile;mp, 146°-150°.

Analysis: Calculated for C₁₆ H₂₃ ClN₆ : C,57.38; H,6.92; N,25.10; Found:C,57.05; H,6.30; N,25.38.

EXAMPLE XXIV4-Chloro-2-(1-cyano-1-methylethylamino)-6-cyclopropylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example X, substitutingcyclopropylamine for isopropylamine. The reaction product wasrecrystallized from a mixture of benzene and methylcyclohexane to give4-chloro-2-(1-cyano-1-methylethylamino)-6-cyclopropylamino-5-pyrimidinecarbonitrile;mp, 174°-177°.

Analysis: Calculated for C₁₂ H₁₃ ClN₆ : C,52.08; H,4.73; N,30.35; Found:C,51.98; H,5.00; N,30.41.

EXAMPLE XXV6-Amino-4-chloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example X, substitutingaqueous 29.8% ammonium hydroxide for isopropylamine. The reactionproduct was recrystallized from benzene to give6-amino-4-chloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile;mp, 193°-198°.

Analysis: Calculated for C₉ H₉ ClN₆ : C,45.67; H,3.83; N,35.51; Found:C,45.66; H,4.07; N,35.57.

EXAMPLE XXVI6-Butylamino-4-chloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example X, substitutingn-butylamine for isopropylamine. The reaction product was recrystallizedfrom methylcyclohexane to give6-butylamino-4-chloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile;mp, 129°-134°.

Analysis: Calculated for C₁₃ H₁₇ ClN₆ : C,53.33; H,5.85; N,28.70; Found:C,53.62; H,5.98; N,28.77.

EXAMPLE XXVII4-Chloro-2-(1-cyano-1-methylpropylamino)-6-cyclopropylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example X, substituting4,6-dichloro-2-(1-cyano-1-methylpropylamino)-5-pyrimidinecarbonitrileand cyclopropylamine for 4,6-dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile andisopropylamine. The reaction product was recrystallized from carbontetrachloride to give4-chloro-2-(1-cyano-1-methylpropylamino)-6-cyclopropylamino-5-pyrimidinecarbonitrile;mp, 155°-159°.

Analysis: Calculated for C₁₃ H₁₅ ClN₆ : C,53.70; H,5.20; N,28.90; Found:C,53.10; H,5.17; N,29.28.

EXAMPLE XXVIII6-Amino-4-chloro-2-isopropylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XVII, substituting4,6-dichloro-2-isopropylamino-5-pyrimidinecarbonitrile and aqueousammonia for 4,6-dichloro-2-ethylamino-5-pyrimidinecarbonitrile andisopropylamine. The reaction product was recrystallized from benzene togive 6-amino-4-chloro-2-isopropylamino-5-pyrimidinecarbonitrile; mp,162°-165°.

Analysis: Calculated for C₈ H₁₀ ClN₅ : C,45.39; H,4.76; N,33.08; Found:C,45.71; H,4.94; N,32.88.

EXAMPLE XXIX4-Chloro-6-cyclopropylamino-2-isopropylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XVII, substituting4,6-dichloro-2-isopropylamino-5-pyrimidinecarbonitrile andcyclopropylamine for 4,6-dichloro-2-ethylamino-5-pyrimidinecarbonitrileand isopropylamine, producing4-chloro-6-cyclopropylamino-2-isopropylamino-5-pyrimidinecarbonitrile.Upon recrystallization from methylcyclohexane, the melting point was157°-160°.

Analysis: Calculated for C₁₁ H₁₄ ClN₅ : C,52.66; H,5.71; N,27.87; Found:C,52.57; H,5.71; N,27.84.

EXAMPLE XXX4-Chloro-6-cyclopropylamino-2-diethylamino-5-pyrimidinecarbonitrile

To a stirred solution of 6.9 grams of4,6-dichloro-2-diethylamino-5-pyrimidinecarbonitrile in 80 ml of acetonewas added dropwise 3.2 grams of cyclopropylamine in 20 ml of acetone.The reaction mixture stood for 16 hours; then the acetone was removed byevaporation under reduced pressure. The residue was washed with water,and the resultant solid was collected. The solid was washed severaltimes with water, then dried, to give 6.5 grams of crude product; mp,100°-105°. The crude product was recrystallized from petroleum ether togive 2.5 grams of4-chloro-6-cyclopropylamino-2-diethylamino-5-pyrimidinecarbonitrile; mp,120°-122°.

Analysis: Calculated for C₁₂ H₁₆ ClN₅ : C,54.23; H,6.06; N,26.35; Found:C,54.12; H,5.99; N,26.43.

EXAMPLE XXXI4-Chloro-6-ethylamino-2-methylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XVII, substituting4,6-dichloro-2-methylamino-5-pyrimidine carbonitrile and aqueous 70%ethylamine for 4,6-dichloro-2-ethylamino-5-pyrimidinecarbonitrile andisopropylamine. The product was4-chloro-6-ethylamino-2-methylamino-5-pyrimidinecarbonitrile; mp,155°-158°.

Analysis: Calculated for C₈ H₁₀ ClN₅ : C,45.5p; H<5>13; N,33.20; Found:C,45.22; H,4.80; N,33.50.

EXAMPLE XXXII 4-Chloro-2,6-bis(isopropylamino)-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XV, substitutingisopropylamine for diethylamine. The reaction product was recrystallizedfrom methylcyclohexane to give4-chloro-2,6-bis(isopropylamino)-5-pyrimidinecarbonitrile; mp, 161°-162°C.

Analysis: Calculated for C₁₁ H₁₆ ClN₅ : C,52.07; H,6.35; N,27.60; Found:C,52.04; H,6.69; N,27.45.

EXAMPLE XXXIII2-(1-Cyano-1-methylethylamino)-6-ethylamino-4-methoxy-5-pyrimidinecarbonitrile

To a stirred solution of 2.7 grams of4-chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrilein 50 ml of methanol was added a solution of 0.3 gram of sodium in 10 mlof methanol. The reaction mixture was heated under reflux for 3 hours.An additional small quantity of sodium in methanol was then added to thereaction mixture, and heating under reflux was continued for 1.5 hours.The excess methanol was removed from the reaction mixture by evaporationunder reduced pressure. The residue was extracted with a mixture ofdiethyl ether and water. The diethyl ether layer was separated, washedwith water, then dried over magnesium sulfate. The mixture was filtered,and the filtrate was evaporated under reduced pressure to a residue. Theresidue was washed with methylcyclohexane, and the insoluble solid wascollected by filtration. The solid was recrystallized from benzene togive 1.7 grams of2-(1-cyano-1-methylethylamino)-6-ethylamino-4-methoxy-5-pyrimidinecarbonitrile;mp, 130°-132°.

Analysis: Calculated for C₁₂ H₁₆ N₆ O: C,55.37; H,6.20 N,32.29; Found:C,55.68; H,6.48; N,32.23.

EXAMPLE XXXIV2-(1-Cyano-1-methylpropylamino)-6-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXIII substituting4-chloro-2-(1-cyano-1-methylpropylamino)-6-isopropylamino-5-pyrimidinecarbonitrilefor4-chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrile.The reaction product was recrystallized from a mixture of benzene andhexane to give2-(1-cyano-1-methylpropylamino)-6-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile;mp, 145°-146°.

Analysis: Calculated for C₁₄ H₂₀ N₆ O: C,58.31; H,6.99; N,29.14; Found:C,58.19; H,6.64; N,28.72.

EXAMPLE XXXV2-(1-Cyano-1-methylethylamino)-6-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile

A solution of 3.8 grams of4-chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrilein methanol was added to a solution of 0.3 gram of sodium in 20 ml ofmethanol. The reaction mixture was heated under reflux for 4 hours, thenallowed to stand at room temperature for 60 hours. The solutionresulting from the addition of 0.05 gram of sodium to 5 ml of methanolwas added to the reaction mixture. The reaction mixture was then heatedunder reflux for 3 hours.

The excess methanol was removed under reduced pressure, and the residuewas extracted with a mixture of diethyl ether and water. The ether layerwas separated and dried over magnesium sulfate. The mixture wasfiltered, and the filtrate was evaporated to dryness under vacuum. Theresidue was recrystallized from a mixture of benzene and petroleum etherto give 1.1 grams of2-(1-cyano-1-methylethylamino)-6-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile;mp, 156°-159°.

Analysis: Calculated for C₁₃ H₁₈ N₆ O: C,56.92; H,6.61; N,30.64; Found:C,57.10; H,6.70; N,30.90.

EXAMPLE XXXVI6-Ethylamino-2-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXIII, substituting4-chloro-6-ethylamino-2-isopropylamino-5-pyrimidinecarbonitrile for4-chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrile.The reaction product was recrystallized from methylcyclohexane, to give6-ethylamino-2-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile; mp,124°-126°.

Analysis: Calculated for C₁₁ H₁₇ N₅ O: C,56.15; H,7.28; N,29.77; Found:C,55.87; H,7.16; N,28.99. EXAMPLE XXXVII

2,6-Bis(ethylamino)-4-methoxy-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXIII, substituting4-chloro-2,6-bis(ethylamino)-5-pyrimidinecarbonitrile for4-chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrile.The reaction product was recrystallized from a mixture of benzene andpetroleum ether, to give2,6-bis(ethylamino)-4-methoxy-5-pyrimidinecarbonitrile; mp, 114°-116°.

Analysis: Calculated for C₁₀ H₁₅ N₅ O: C,54.28; H,6.83; N,31.66; Found:C,54.38; H,7.08; N,31.93.

EXAMPLE XXXVIII 2,6-Bis(diethylamino)-4-methoxy-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXIII,substitutiting 4-chloro-2,6-bis(diethylamino)-5- pyrimidinecarbonitrilefor4-chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrile.The reaction product was recrystallized from petroleum ether to give2,6-bis(diethylamino)-4-methoxy-5-pyrimidinecarbonitrile; mp, 37°-39°.

Analysis: Calculated for C₁₄ H₂₃ N₅ O: C,60.62; H,8.36; N,25.25; Found:C,60.92; H,8.40; N,25.60.

EXAMPLE XXXIX6-Diethylamino-2-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXV, substituting4-chloro-6-diethylamino-2-isopropylamino-5-pyrimidinecarbonitrile for4-chloro-2-(1═cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile.It yielded of liquid6-diethylamino-2-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile.

Analysis: Calculated for C₁₃ H₂₁ N₅ O: C,59.29; H,8.04; N,26.60; Found:C,59.00; H,8.33; N,26.36.

EXAMPLE XL2-Ethylamino-6-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXV, substituting4-chloro-2-ethylamino-6-isopropylamino-5-pyrimidinecarbonitrile for4-chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile.The product was2-ethylamino-6-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile; mp,125°-128°.

Analysis: Calculated for C₁₁ H₁₇ N₅ O: C,56.15; H,7.28; N,29.76; Found:C,56.12; H,6.99; N,29.75.

EXAMPLE XLI4-Ethoxy-6-ethylamino-2-isopropylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXIII, substituting4-chloro-6-ethylamino-2-isopropylamino-5-pyrimidinecarbonitrile and asolution of sodium in ethanol for4-chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrileand a solution of sodium in methanol. The reaction product wasrecrystallized from petroleum ether to give4-ethoxy-6-ethylamino-2-isopropylamino-5-pyrimidinecarbonitrile; mp,98°-99°.

Analysis: Calculated for C₁₂ H₁₉ N₅ O: C,57.81; H,7.68; N,28.09; Found:C,57.89; H,7.59; N,28.18.

EXAMPLE XLII6-Ethylamino-4-methoxy-2-methylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXV, substituting4-chloro-6-ethylamino-2-methylamino-5-pyrimidinecarbonitrile for4-chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile.The product was6-ethylamino-4-methoxy-2-methylamino-5-pyrimidinecarbonitrile; mp,147°-149°.

Analysis: Calculated for C₉ H₁₃ N₅ O: C,52.16; H,6.32; N,33.80; Found:C,52.08; H,6.60; N,34.07.

EXAMPLE XLIII6-Isopropylamino-4-methoxy-2-methylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXV, substituting4-chloro-6-isopropylamino-2-methylamino-5-pyrimidinecarbonitrile for4-chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile.The product was6-isopropylamino-4-methoxy-2-methylamino-5-pyrimidinecarbonitrile; mp,112°-115°.

Analysis: Calculated for C₁₀ H₁₅ N₅ O: C,54.28; H,6.83; N,31.66; Found:C,53.14; H,6.61; N,32.26.

EXAMPLE XLIV2-Isopropylamino-4-methoxy-6-methylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXV, substituting4-chloro-2-isopropylamino-6-methylamino-5-pyrimidinecarbonitrile for4-chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile.The product was2-isopropylamino-4-methoxy-6-methylamino-5-pyrimidinecarbonitrile; mp,134°-137°.

Analysis: Calculated for C₁₀ H₁₅ N₅ O: C,54.28; H,6.83; N,31.66; Found:C,53.63; H,6.50; N,31.88.

EXAMPLE XLV6-Diethylamino-2-ethylamino-4-methoxy-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXV, substituting4-chloro-6-diethylamino-2-ethylamino-5-pyrimidinecarbonitrile for4-chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile.The product was6-diethylamino-2-ethylamino-4-methoxy-5-pyrimidinecarbonitrile; mp,73°-75°.

Analysis: Calculated for C₁₂ H₁₈ N₅ O: C,57.81; H,7.68; N,28.09; Found:C,57.67; H,7.46; N,28.26.

EXAMPLE XLVI4-Ethoxy-6-diethylamino-2-isopropylamino-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXIII, substituting4-chloro-6-diethylamino-2-isopropylamino-5-pyrimidinecarbonitrile and asolution of sodium in ethanol for2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrile anda solution of sodium in methanol. The reaction product wasrecrystallized from hexane to give4-ethoxy-6-diethylamino-2-isopropylamino-5-pyrimidinecarbonitrile; mp,55°-57°.

Analysis: Calculated for C₁₄ H₂₃ N₅ O: C,60.62; H,8.36; N,25.25; Found:C,60.32; H,8.33; N,25.30.

EXAMPLE XLVII2-(1-Cyano-1-methylethylamino)-4-methoxy-6-(1-methylbutylamino)-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXV, substituting4-chloro-2-(1-cyano-1-methylethylamino)-6-(1-methylbutylamino)-5-pyrimidinecarbonitrilefor4-chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile.The reaction product was recrystallized twice from methylcyclohexane togive2-(1-cyano-1-methylethylamino)-4-methoxy-6-(1-methylbutylamino)-5-pyrimidinecarbonitrile;mp, 142°-147°.

Analysis: Calculated for C₁₅ H₂₂ N₆ O: C,59.58; H,7.33; N,27.80; Found:C,59.43; H,7.59; N,27.75.

EXAMPLE XLVIII2-(1-Cyano-1-methylethylamino)-6-(1-isopropyl-2-methylpropylamino)-4-methoxy-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXV, substituting4-chloro-2-(1-cyano-1-methylethylamino)-6-(1-isopropyl-2-methylpropylamino)-5-pyrimidinecarbonitrilefor4-chloro-2-(1-cyano-1-methylethylamino)-6-ispropylamino-5-pyrimidinecarbonitrile.The reaction product was recrystallized from methylcyclohexane to give2-(1-cyano-1-methylethylamino)6-(1-isopropyl-2-methylpropylamino)-4-methoxy-5-pyrimidinecarbonitrile;mp, 121°-124°.

Analysis: Calculated for C₁₇ H₂₆ N₆ O: C,61.79; H,7.93; N,25.44; Found:C,61.49; H,7.73; N,25.67.

EXAMPLE XLIX2-(1-Cyano-1-methylethylamino)-6-cyclopropylamino-4-methoxy-5-pyrimidinecarbonitrile

To a stirred solution of 0.8 gram of sodium methoxide in 100 ml ofmethanol was added portionwise 4.2 gramsof4-chloro-2-(1-cyano-1-methylethylamino)-6-cyclopropylamino-5-pyrimidinecarbonitrile.Upon complete addition, the reaction mixture was heated under reflux for3.5 hours, then allowed to stand at room temperature for 16 hours. Themethanol was removed by evaporation under reduced pressure. The residuewas extracted with a mixture of water and methylene chloride. Themethylene chloride layer was separated and dried over magnesium sulfate.The mixture was filtered, and the filtrate was evaporated under reducedpressure. The residue was recrystallized twice from carbon tetrachlorideto give 2.4 grams of2-(1-cyano-1-methylethylamino)-6-cyclopropylamino-4-methoxy-5-pyrimidinecarbonitrile;mp, 138°-140°.

Analysis: Calculated for C₁₃ H₁₆ N₆ O: C,57.33; H,5.93; N,30.86; Found:C,57.21; H,5.99; N,30.84.

EXAMPLE L6-Amino-2-(1-cyano-1-methylethylamino)-4-methoxy-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXIII, substituting6-amino4-chloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrilefor4-chloro-2-(1-cyano-1-methylethylamino)-6-ethylamino-5-pyrimidinecarbonitrile.The reaction product was recrystallized from anhydrous ethanol to give6-amino-2-(1-cyano-1-methylethylamino)-4-methoxy-5-pyrimidinecarbonitrile;mp, 240°-243°.

Analysis: Calculated for C₁₀ H₁₂ N₆ O: C,51.71; H,5.21; N,36.19; Found:C,51.70; H,5.51; N,36.47.

EXAMPLE LI6-Butylamino-2-(1-cyano-1-methylethylamino)4-methoxy-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXV, substituting6-butylamino-4-chloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrilefor4-chloro-2-(1-cyano-1-methylethylamino)6-isopropylamino-5-pyrimidinecarbonitrile.The reaction product was recrystallized from methylcyclohexane to give6-butylamino-2-(1-cyano-1-methylethylethylamino)-4-methoxy-5-pyrimidinecarbonitrile;mp, 120°-127°.

Analysis: Calculated for C₁₄ H₂₀ N₆ O: C,58.31; H,6.99; N,29.14; Found:C,57.87; H,6.69; N,29.48.

EXAMPLE LII2-(1-Cyano-1-methylpropylamino)-6-cyclopropylamino-4-methoxy-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXV, substituting4-chloro-2-(1-cyano-1-methylpropylamino)-6-cyclopropylamino-5-pyrimidinecarbonitrilefor4-chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile.The reaction product was recrystallized from a mixture of benzene andmethylcyclohexane to give2-(1-cyano-1-methylpropylamino)-6-cyclopropylamino-4-methoxy-5-pyrimidinecarbonitrile;mp, 114°-118°.

Analysis: Calculated for C₁₄ H₁₈ N₆ O: C,58.73; H,6.34; N,29.35; Found:C,58.70; H,6.55; N,29.35.

EXAMPLE LIII 6-Amino-2-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXV, substituting6-amino-4-chloro-2-isopropylamino-5-pyrimidinecarbonitrile for4-chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile.The product was6-amino-2-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile; mp,224°-227°.

Analysis: Calculated for C₉ H₁₃ N₅ O: C,52.16; H,6.32; N,33.80; Found:C,51.80; H,6.39; N,33.87.

EXAMPLE LIV6-Cyclopropylamino-2-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile

To a stirred solution of 0.9 gram of sodium methoxide in 100 ml ofmethanol was added, in one portion, 4.0 grams of4-chloro-6-cyclopropylamino-2-isopropylamino-5-pyrimidinecarbonitrile.The reaction mixture was then heated under reflux for 3 hours. Themethanol was removed by evaporation under reduced pressure to give aresidue. The residue was washed with water, and the solid was collectedby filtration to yield 3.5 grams of6-cyclopropylamino-2-isopropylamino-4-methoxy-5- pyrimidinecarbonitrile;mp, 142°-147°.

Analysis: Calculated for C₁₂ H₁₇ N₅ O; C,58.28; H,6.92; N,28.31; Found:C,58.04; H,6.98; N,28.34.

EXAMPLE LV6-Cyclopropylamino-2-diethylamino-4-methoxy-5-pyrimidinecarbonitrile

This compound was prepared in the manner of Example XXXV, substituting4-chloro-6-cyclopropylamino-2-diethylamino-5-pyrimidinecarbonitrile for4-chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile,to produce6-cyclopropylamino-2-diethylamino-4-methoxy-5-pyrimidinecarbonitrile.Upon recrystallization from methylcyclohexane, the melting point was146°-150°.

Analysis: Calculated for C₁₃ H₁₄ N₅ O: C,59.15; H,7.33; N,26.80; Found:C,59.02; H,7.05; N,26.79.

EXAMPLE LVI 2,6-Bis(isopropylamino)-4-methoxy-5-pyrimidinecarbonitrile

To a solution of 6.3 grams of4-chloro-2,6-bis(isopropylamino)-5-pyrimidinecarbonitrile in 100 ml ofmethanol was added a solution of methanolic sodium methoxide (0.805grams of sodium in 50 ml of methanol). After complete addition, thereaction mixture was stirred for 16 hours. The reaction mixture was thenheated under reflux for 5 hours. The excess methanol was removed underreduced pressure. The residue was extracted with a mixture of diethylether and water. The organic layer was separated and dried overmagnesium sulfate. The mixture was filtered, and the filtrate wasevaporated to dryness under reduced pressure. The residue wasrecrystallized from cyclohexane, to give 4.5 grams of2,6-bis(isopropylamino)-4-methoxy-5-pyrimidinecarbonitrile; mp,131°-133°.

Analysis: Calculated for C₁₂ H₁₉ N₅ O: C,57.81; H,7.68; N,28.09; Found:C,57.57; H,7.62; N,28.15.

EXAMPLE LVII 4-Methoxy-2,6-bis(methylamino)-5-pyrimidinecarbonitrile

This compound, mp, 177°-179°, was prepared by the method of ExampleXXXV, substituting4-chloro-2,6-bis(methylamino)-5-pyrimidinecarbonitrile for4-chloro-2-(1-cyano-1-methylethylamino)-6-isopropylamino-5-pyrimidinecarbonitrile.

EXAMPLE LVIII2-Cyclopropylamino-6-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile

4-Chloro-2-cyclopropylamino-6-isopropylamino-5-pyrimidinecarbonitrilewas prepared by the method of Example XVII, substituting2,4-dichloro-6-isopropylamino-5-pyrimidinecarbonitrile (isolated from amixture of 2,4-dichloro-6-isopropylamino-5-pyrimidinecarbonitrile and4,6-dichloro-2-isopropylamino-5-pyrimidinecarbonitrile), andcyclopropylamine for 4,6-dichloro-2-ethylamino-5-pyrimidinecarbonitrileand isopropylamine. The reaction product was recrystallized from benzeneto give4-chloro-2-cyclopropylamino-6-isopropylamino-5-pyrimidinecarbonitrile;mp, 212°-215°.

Analysis: Calculated for C₁₁ H₁₄ ClN₅ : C,52.48; H,5.61; N,27.82; Found:C,52.69; H,5.77; N,28.05.

2-Cyclopropylamino-6-isopropylamino-4-methoxy-5-pyrimidinecarbonitrilewas then prepared by the method of Example LIV, substituting4-chloro-2-cyclopropylamino-6-isopropylamino-5-pyrimidinecarbonitrilefor4-chloro-6-cyclopropylamino-2-isopropylamino-5-pyrimidinecarbonitrile.The reaction product was recrystallized from methylcyclohexane to give2-cyclopropylamino-6-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile;mp, 108°-111°.

Analysis: Calculated for C₁₂ H₁₇ N₅ O: C,58.28; H,6.93; N,28.32; Found:C,58.70; H,6.78; N,28.66.

EXAMPLE LIX 2,6-Bis(cyclopropylamino)-4-methoxy-5-pyrimidinecarbonitrile

4-Chloro-2,6-bis(cyclopropylamino)-5-pyrimidinecarbonitrile was preparedby the method of Example XIV, substituting cyclopropylamine for 70%ethylamine. The reaction product was recrystallized from a mixture ofbenzene and methylcyclohexane to give4-chloro-2,6-bis(cyclopropylamino)-5-pyrimidinecarbonitrile; mp,210°-215°.

Analysis: Calculated for C₁₁ H₁₂ ClN₅ : C,52.91; H,4.84; N,28.04; Found:C,52.53; H,4.99; N,27.67.

2,6-Bis(cyclopropylamino)-4-methoxy-5-pyrimidinecarbonitrile was thenprepared by the method of Example LIV, substituting4-chloro-2,6-bis(cyclopropylamino)-5-pyrimidinecarbonitrile for4-chloro-6-cyclopropylamino-2-isopropylamino-5-pyrimidinecarbonitrile.The reaction product was recrystallized from methylcyclohexane to give2,6-bis(cyclopropylamino)-4-methoxy-5-pyrimidinecarbonitrile; mp,130°-135°.

Analysis: Calculated for C₁₂ H₁₅ N₅ O: C,58.76; H,6.16; N,28.56; Found:C,58.71; H,6.53; N,28.75.

EXAMPLE LX6-Cyclopropylamino-4-methoxy-2-(1-methylpropylamino)-5-pyrimidinecarbonitrile

4,6-Dichloro-2-(1-methylpropylamino)-5-pyrimidinecarbonitrile wasprepared by the method of Example V, substituting 1-methylpropylaminefor 70% ethylamine. The reaction product was recrystallized frommethylcyclohexane, then from a mixture of benzene and hexane to give4,6-dichloro-2-(1-methylpropylamino)-5-pyrimidinecarbonitrile; mp,110°-120°.

Analysis: Calculated for C₉ H₁₀ Cl₂ N₄ : C,44.10; H,4.11; N,22.86;Found: C,44.34; H,4.43; N,22.88.

4-Chloro-6-cyclopropylamino-2-(1-methylpropylamino)-5-pyrimidinecarbonitrilewas prepared by the method of Example XVII, substituting4,6-dichloro-2-(1-methylpropylamino)-5-pyrimidinecarbonitrile andcyclopropylamine for 4,6-dichloro-2-ethylamino-5-pyrimidinecarbonitrileand isopropylamine. The reaction product was recrystallized frommethylcyclohexane to give4-chloro-6-cyclopropylamino-2-(1-methylpropylamino)-5-pyrimidinecarbonitrile;mp, 112°-114°.

Analysis: Calculated for C₁₂ H₁₆ ClN₅ : C,54.24; H,6.07; N,26.35; Found:C,54.13; H,6.25; N,26.38.

6-Cyclopropylamino-4-methoxy-2-(1-methylpropylamino)-5-pyrimidinecarbonitrilewas prepared in the manner of Example LIV, substituting4-chloro-6-cyclopropylamino-2-(1-methylpropylamino)-5-pyrimidinecarbonitrilefor4-chloro-6-cyclopropylamino-2-isopropylamino-5-pyrimidinecarbonitrile.The reaction product was recrystallized from methylcyclohexane to give6-cyclopropylamino-4-methoxy-2-(1-methylpropylamino)-5-pyrimidinecarbonitrile;mp, 120°-123°.

Analysis: Calculated for C₁₃ H₁₉ N₅ O: C,59.75; H,7.33; N,26.80; Found:C,59.26; H,7.39; N,26.61.

EXAMPLE LXI4-Methoxy-6-(1-methylethylamino)-2-(2-methylpropylamino)-5-pyrimidinecarbonitrile

4,6-Dichloro-2-(2-methylpropylamino)-5-pyrimidinecarbonitrile wasprepared by the method of Example V, substituting 2-methylpropylaminefor 70% ethylamine. The reaction product was recrystallized from amixture of benzene and methylcyclohexane to give4,6-dichloro-2-(2-methylpropylamino)-5-pyrimidinecarbonitrile; mp,137°-150°.

Analysis: Calculated for C₉ H₁₀ Cl₂ N₄ : C,44.10; H,4.11; N,22.86;Found: C,43.62; H,4.08; N,22.67.

4-Chloro-6-(1-methylethylamino)-2-(2-methylpropylamino)-5-pyrimidinecarbonitrilewas prepared by the method of Example XVII, substituting4,6-dichloro-2-(2-methylpropylamino)-5-pyrimidinecarbonitrile for4,6-dichloro-2-ethylamino-5-pyrimidinecarbonitrile. The reaction productwas recrystallized from methylcyclohexane to give4-chloro-6-(1-methylethylamino)-2-(2-methylpropylamino)-5-pyrimidinecarbonitrile;mp, 170°-172°.

Analysis: Calculated for C₁₂ H₁₈ ClN₅ : C,53.82; H,6.77; N,26.16; Found:C,53.79; H,6.95; N,26.41.

4-Methoxy-6-(1-methylethylamino)-2-(2-methylpropyl-amino)-5-pyrimidinecarbonitrilewas prepared in the manner of Example LIV, substituting4-chloro-6-(1-methylethylamino)-2-(2-methylpropylamino)-5-pyrimidinecarbonitrilefor4-chloro-6-cyclopropylamino-2-isopropylamino-5-pyrimidinecarbonitrile.The reaction product was recrystallized from methylcyclohexane to give4-methoxy-6-(1-methylethylamino)-2-(2-methylpropylamino)-5-pyrimidinecarbonitrile;mp, 99°-101°.

Analysis: Calculated for C₁₃ H₂₁ N₅ O: C,59.29; H,8.04; N,26.16; Found:C,59.15; H,7.68; N,25.79.

The ability of the herbicidally active compounds to control undesiredplant growth was demonstrated as follows:

For preemergence tests, rows of the seeds of lima bean (Phaseoluslunatus), corn (Zea mays), wild oats (Avena fatua), lettuce (Lactucasativa), mustard (Brassica juncea) and crabgrass (Digitaria sanguinalis)were planted together in 15 cm by 20 cm by 8 cm flats containingapproximately 5 cm of sandy loam soil. After planting, an aqueousacetone solution of one of the active compounds was sprayed directly onthe soil and exposed seeds, the active compound being applied uniformlyat 8.96 kg per hectare. A thin layer of soil, approximately 1.3 cm deep,was then applied over the seeds. The flats were maintained in agreenhouse, and watered regularly on the surface of the soil for 10-14days. At the end of this period, the phytotoxicity of the compound wasrecorded. Individual plant species were examined for percent kill, and avigor rating of 0 to 5 was assigned to the surviving plants, a vigorrating of 5 signifying no chemical injury, 4- slight injury (plants haveor are expected to recover), 3- moderate to severe injury (plantsexpected to recover in time), 2- moderate to severe injury (plants notexpected to recover), 1- severe injury (plants not expected to recover),and 0- complete kill. Table 1 lists data collected in preemergence testswith herbicidally active compounds of the present invention.

                                      TABLE 1                                     __________________________________________________________________________    PREEMERGENCE HERBICIDAL ACTIVITY OF 5-PYRIMIDINE-                             CARBONITRILES*                                                                Active Compound                                                                        Lima Bean                                                                           Corn                                                                              Wild Oats                                                                           Lettuce                                                                            Mustard                                                                            Crabgrass                                  of Example                                                                             K  V  K V K.sup.a                                                                             K  V K  V K  V                                       __________________________________________________________________________    XXXIII   0  3  0 3 0     100                                                                              0 100                                                                              0 80 2                                       XXXIV    0  2  0 2 0     100                                                                              0 100                                                                              0 100                                                                              0                                       XXXV     0  5  0 4 0     0  4 30 4 0  4                                       XXXVI    0  4  0 3 0     90 1 90 1 90 1                                       XXXVII   0  5  0 4 0     60 4 100                                                                              0 90 1                                       XXXVIII  0  5  0 5 0     0  5 0  4 90 1                                       XXXIX    0  5  0 5 0     0  4 80 2 0  4                                       XL       0  5  0 5 0     0  4 0  4 0  4                                       XLI      0  5  0 5 0     100                                                                              0 100                                                                              0 100                                                                              0                                       XLII     0  5  0 5 0     0  3 100                                                                              0 80 2                                       XLIII    0  5  0 5 0     0  4 80 2 90 1                                       XLIV     0  4  0 5 0     0  5 0  5 0  4                                       XLV      0  5  0 5 0     80 3 100                                                                              0 100                                                                              0                                       XLVII    0  5  0 5 0     0  4 90 1 0  4                                       XLVIII   0  5  0 5 0     0  5 90 1 50 3                                       XLIX     100                                                                              0  0 2 0     100                                                                              0 100                                                                              0 85 2                                       LIII     0  3  0 4 0     0  2 80 2 0  3                                       LVI      0  4  0 4 0     0  3 0  3 0  3                                       LVII     0  5  0 5 0     0  4 40 4 0  4                                       __________________________________________________________________________     *Entries under K refer to percent kill; under V, to plant vigor, a vigor      of 5 signifying no chemical injury. 5Pyrimidinecarbonitrile applied           uniformly at 8.96 kg per hectare.                                             .sup.a Surviving plants expected to recover.                             

In postemergence tests, untreated plants prepared as described abovewere maintained in a greenhouse and watered regularly for a period of10-14 days, until the first trifoliate leaves of the bean plants wereunfolding. The plants were then sprayed uniformly with an aqueousacetone solution of one of the herbicidally active compounds at 8.96 kgper hectare as in the preemergence tests. The treated plants weremaintained in a greenhouse and watered regularly for an additional 10-14days. At the end of that time the phytotoxicity of the compound wasrecorded as in the preemergence tests. The results of these tests appearin Table 2.

                                      TABLE 2                                     __________________________________________________________________________    POSTEMERGENCE HERBICIDAL ACTIVITY OF 5-PYRIMIDINE-                            CARBONITRILES*                                                                Active Compound                                                                        Lima Bean                                                                           Corn Wild Oats                                                                           Lettuce                                                                            Mustard                                                                            Crabgrass                                 of Example                                                                             K  V  K  V K  V  K  V K  V K  V                                      __________________________________________________________________________    XXXIII   0  4  0  5 0  4  100                                                                              0 100                                                                              0 0  5                                      XXXIV    100                                                                              0  0  5 0  5  100                                                                              0 100                                                                              0 100                                                                              0                                      XXXV     100                                                                              0  100                                                                              0 100                                                                              0  100                                                                              0 100                                                                              0 100                                                                              0                                      XXXVI    100                                                                              0  0  4 80 2  100                                                                              0 100                                                                              0 100                                                                              0                                      XXXVII   0  3  0  3 100                                                                              0  100                                                                              0 100                                                                              0 100                                                                              0                                      XXXVIII  0  3  75 3 100                                                                              0  100                                                                              0 90 1 90 1                                      XXXIX    0  4  0  3 90 1  100                                                                              0 100                                                                              0 100                                                                              0                                      XL       0  4  0  5 0  5  90 1 90 1 100                                                                              0                                      XLI      100                                                                              0  0  5 50 4  100                                                                              0 100                                                                              0 100                                                                              0                                      XLII     0  4  0  5 0  4  90 1 100                                                                              0 90 1                                      XLIII    0  4  75 1 0  4  80 2 100                                                                              0 85 2                                      XLIV     0  2  0  5 0  3  100                                                                              0 100                                                                              0 100                                                                              0                                      XLV      100                                                                              0  25 4 0  3  100                                                                              0 100                                                                              0 100                                                                              0                                      XLVII    50 3  0  5 0  5  100                                                                              0 100                                                                              0 100                                                                              0                                      XLVIII   0  5  0  5 0  5  100                                                                              0 100                                                                              0 100                                                                              0                                      XLIX     100                                                                              0  100                                                                              0 100                                                                              0  100                                                                              0 100                                                                              0 100                                                                              0                                      LIII     0  3  0  5 0  5  0  4 39 4 80 2                                      LVI      0  3  0  5 0  4  50 2 0  3 0  4                                      LVII     0  5  0  5 0  5  0  5 0  5 0  5                                      __________________________________________________________________________     *Entries under K refer to percent kill; under V, to plant vigor, a vigor      or 5 signifying no chemical injury. 5Pyrimidinecarbonitrile applied           uniformly at 8.96 kg per hectare.                                        

The effect of the amount of active compound applied per hectare uponperformance as a preemergence herbicide was determined for several5-pyrimidinecarbonitriles. The evaluations were conducted as describedabove, except that additional plant species were included in someinstances, and various rates of application ranging downward from 8.96kg per hectare were employed. The following plant species were added insome tests: sugarbeen (Beta vulgaris); onion (Allium cepa); greenfoxtain (Setaria viridis); soybean (Glycine max); cotton (Gossypiumhirsutum); sorghum (Sorghum vulgare); sicklepod (Cassia obtusifolia);barley (Hordeum vulgare); barnyardgrass (Echinochloa crusgalli); peanut(Arachis hypogaea); safflower (Carthamus tinctorius); tomato(Lycopersicon esculentum); flax (Linum usitatissimum); rice (Oryzasativa); wheat (Triticum aestivium); cocklebur (Xanthium pensylvanicum);pigweed (Amaranthus retroflexus); morningglory (Ipomoea purpurea); rape(Brassica campestris); prickly sida (Sida spinosa L.); lambsquarter(Chenopodium album). The results of these tests appear in Tables 3through 21.

                  TABLE 3                                                         ______________________________________                                        EFFECT OF APPLICATION LEVEL ON                                                PREEMERGENCE PERFORMANCE OF 2-(1-CYANO-1-                                     METHYL-ETHYLAMINO)-6-ETHYLAMINO-4-METHOXY-5-                                  PYRIMIDINECARBONITRILE (Example XXXIII)*                                              0.14  0.28    0.56     1.12   2.24                                            kg/ha kg/ha   kg/ha    kg/ha  kg/ha                                   Crop      K.sup.a K     V   K    V   K    V   K    V                          ______________________________________                                        Lima Bean 0       0     5   0    5   25   4   100  0                          Corn      0       0     5   0    5   0    5   0    5                          Wild Oat  0       0     5   0    5   20   4   20   4                          Sugarbeet 0       0     5   30   4   100  0   100  0                          Onion     25      25    4   50   4   100  0   100  0                          Green Foxtail                                                                           0       0     5   0    4   60   3   100  0                          Soybean   0       0     5   0    5   0    4   75   3                          Cotton    0       0     5   0    5   0    5   0    5                          Sorghum   0       0     5   0    5   50   4   90   3                          Sicklepod 0       0     5   0    5   0    5   0    4                          Barley    0       0     5   0    5   10   4   75   4                          Barnyardgrass                                                                           0       0     5   0    5   25   4   100  0                          Peanut    0       0     5   0    5   0    5   0    5                          Safflower 0       0     5   0    5   10   4   50   4                          Tomato    0       0     5   0    5   80   4   100  0                          Flax      0       0     5   50   4   90   2   100  0                          Rice      0       0     5   0    5   0    5   100  0                          Wheat     0       0     5   0    5   10   4   75   4                          Nutsedge  0       0     5   0    5   0    5   0    5                          Lettuce   --      20    4   80   3   100  0   100  0                          Mustard   --      95    1   100  0   100  0   100  0                          Crabgrass --      90    1   90   1   100  0   100  0                          ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      of 5 signifying no chemical injury.                                           .sup.a Surviving plants expected to recover.                             

                  TABLE 4                                                         ______________________________________                                        EFFECT OF APPLICATION LEVEL ON PREEMER-                                       GENCE PERFORMANCE OF 2-(1-CYANO-1-METHYL-                                     PROPYLAMINO)-6-ISOPROPYLAMINO-4-METHOXY-5-                                    PYRIMIDINECARBONITRILE (Example XXXIV)*                                                     0.56    1.12     2.24   4.48                                    0.28 kg/ha    kg/ha   kg/ha    kg/ha  kg/ha                                   Crop    K.sup.a   K     V   K    V   K    V   K    V                          ______________________________________                                        Lima Bean                                                                             0         0     5   0    4   0    4   50   2                          Corn    0         0     5   0    5   0    5   0    5                          Wild Oats                                                                             0         0     5   0    5   20   4   75   3                          Lettuce 0         75    4   100  0   100  0   100  0                          Mustard 0         75    2   90   1   100  0   100  0                          Crabgrass                                                                             0         60    4   80   1   100  0   100  0                          ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      of 5 signifying no chemical injury.                                           .sup.a Surviving plants expected to recover.                             

                  TABLE 5                                                         ______________________________________                                        EFFECT OF APPLICATION LEVEL ON PREEMER-                                       GENCE PERFORMANCE OF 2-(1-CYANO-1-METHYL-                                     ETHYLAMINO)-6-ISOPROPYLAMINO-4-METHOXY-5-                                     PYRIMIDINECARBONITRILE (Example XXXV)*                                                 0.28                                                                          kg/ha 0.56 kg/ha                                                                              1.12 kg/ha                                                                              2.24 kg/hz                                 CROP       K.sup.a K.sup.a   K    V    K    V                                 ______________________________________                                        Lima Bean  0       0         0    5    100  0                                 Corn       0       0         0    5    30   0                                 Wild Oats  0       0         0    5    0    5                                 Sugarbeet  0       10        100  0    100  0                                 Onion      30      75        100  0    100  0                                 Green Foxtail                                                                            0       0         50   4    100  0                                 Soybean    0       0         0    5    0    5                                 Cotton     0       0         0    5    0    5                                 Sorghum    0       0         0    5    0    5                                 Sicklepod  0       0         0    5    0    5                                 Barley     0       0         30   4    100  0                                 Barnyardgrass                                                                            0       0         10   4    100  0                                 Peanut     0       0         0    5    0    5                                 Safflower  0       0         0    5    0    4                                 Tomato     0       0         25   4    100  0                                 Flax       0       0         50   4    100  0                                 Rice       0       0         0    5    50   4                                 Wheat      0       0         10   4    75   3                                 Nutsedge   0       0         0    5    0    5                                 ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                                    .sup.a Surviving plants expected to recover.                             

                  TABLE 6                                                         ______________________________________                                        EFFECT OF APPLICATION LEVEL ON PREEMER-                                       GENCE PERFORMANCE OF 6-ETHYLAMINO-2-ISO-                                      PROPYLAMINO-4-METHOXY-5-PYRIMIDINE-                                           CARBONITRILE (Example XXXVI)*                                                          2.24 kg/ha                                                                            4.48 kg/ha 8.96 kg/ha                                        CROP       K.sup.a   K.sup.a    K    V                                        ______________________________________                                        Lima Bean  0         0          0    5                                        Corn       0         0          0    4                                        Wild Oats  0         0          0    3                                        Lettuce    0         25         75   2                                        Mustard    0         40         90   1                                        Crabgrass  0         0          0    2                                        Nutsedge   0         0          0    5                                        ______________________________________                                         *Entries under K refer to percent kill; under V to plant vigor, a vigor o     5 signifying no chemical injury.                                              .sup.a Surviving plants are expected to recover.                         

                  TABLE 7                                                         ______________________________________                                        EFFECT OF APPLICATION                                                         LEVEL ON PREEMERGENCE                                                         PERFORMANCE OF 6-ETHYLAMINO-4-METHOXY-2-                                      METHYLAMINO-5-PYRIMIDINECARBONITRILE                                          (EXAMPLE XLII)*                                                                        2.24 kg/ha   4.48 kg/ha                                              CROP       K.sup.a        K      V                                            ______________________________________                                        Lima Bean  50             100    0                                            Corn       0              0      5                                            Wild Oats  0              0      4                                            Lettuce    0              25     4                                            Mustard    0              90     1                                            Crabgrass  0              75     2                                            Nutsedge   0              0      5                                            ______________________________________                                         *Entries under K refer to percent kill; under V to plant vigor, a vigor o     5 signifying no chemical injury.                                              .sup.a Surviving plants expected to recover.                             

                  TABLE 8                                                         ______________________________________                                        EFFECT OF APPLICATION                                                         LEVEL ON PREEMERGENCE                                                         PERFORMANCE OF 6-ISOPROPYLAMINO-4-METHOXY-                                    2-METHYLAMINO-5-PYRIMIDINECARBONITRILE                                        (Example XLIII)*                                                                      2.24 kg/ha                                                                             4.48 kg/ha 8.96 kg/ha                                        CROP      K.sup.a    K      V     K    V                                      ______________________________________                                        Lima Bean 0          0      5     0    4                                      Corn      0          0      5     0    5                                      Wild Oats 0          0      5     0    5                                      Lettuce   0          30     4     10   4                                      Mustard   0          30     4     40   4                                      Crabgrass 0          75     2     75   2                                      Nutsedge  0          0      5     9    5                                      ______________________________________                                         Entries under K refer to percent kill; under V, to plant vigor, a vigor       rating of 5 signifying no chemical injury.                                    .sup.a Surviving plants expected to recover.                             

                  TABLE 9                                                         ______________________________________                                        EFFECT OF APPLICATION                                                         LEVEL ON PREEMERGENCE                                                         PERFORMANCE OF 6-DIETHYLAMINO-2-ETHYLAMINO-                                   4-METHOXY-5-PYRIMIDINECARBONITRILE                                            (Example XLV)*                                                                         4.48 kg/ha   8.96 kg/ha                                              CROP       K.sup.a        K      V                                            ______________________________________                                        Lima Beans 0              0      5                                            Corn       0              0      5                                            Wild Oats  0              0      5                                            Lettuce    0              10     4                                            Mustard    30             100    0                                            Crabgrass  0              90     1                                            Nutsedge   0              0      5                                            ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                                    .sup.a Surviving plants expected to recover.                             

                  TABLE 10                                                        ______________________________________                                        EFFECT OF APPLICATION                                                         LEVEL ON PREEMERGENCE                                                         PERFORMANCE OF 4-ETHOXY-6-DIETHYLAMINO-2-                                     ISOPROPYLAMINO-5-PYRIMIDINECARBONITRILE                                       (Example XLVI)*                                                                             2.24 kg/ha                                                                            4.48 kg/ha                                              CROP            K.sup.a   K.sup.a                                             ______________________________________                                        Lima Beans      0         0                                                   Corn            0         0                                                   Wild Oat        0         0                                                   Lettuce         0         0                                                   Mustard         0         0                                                   Crabgrass       0         0                                                   Soybean         0         0                                                   Cotton          0         0                                                   Flax            0         0                                                   Peanut          0         0                                                   Rice            0         0                                                   Sugarbeet       0         0                                                   Rape            0         0                                                   Foxtail         0         0                                                   Sorghum         0         0                                                   Barnyardgrass   0         0                                                   Onion           20        75                                                  Safflower       0         0                                                   Prickly Sida    0         0                                                   Morningglory    0         0                                                   Tomato          0         0                                                   Nutsedge        0         0                                                   ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                                    .sup.a Surviving plants expected to recover.                             

                  TABLE 11                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON PREEMERGENCE                                   PERFORMANCE OF 2-(1-CYANO-1-METHYLETHYL-                                      AMINO)-4-METHOXY-6-(1-METHYLBUTYLAMINO)-5-                                    PYRIMIDINE-CARBONITRILE                                                       (Example XLVII)*                                                                      0.28                                                                          kg/  0.56 kg/ 1.12 kg/ 2.24 kg/                                                                             4.48 kg/                                        ha   ha       ha       ha     ha                                      CROP      K.sup.a                                                                              K      V   K    V   K    V   K    V                          ______________________________________                                        Rice      0      0      5   0    5   0    5   0    5                          Flax      0      0      5   0    5   0    5   0    5                          Safflower 0      0      5   0    5   0    5   0    5                          Tomato    0      0      5   0    5   0    5   0    5                          Peanut    0      0      5   0    5   0    5   0    5                          Wheat     0      0      5   0    5   0    5   0    5                          Morningglory                                                                            0      0      5   0    5   0    5   0    5                          Sugarbeet 0      100    0   100  0   100  0   100  0                          Lima Bean 0      0      5   0    5   0    5   0    5                          Corn      0      0      5   0    5   0    5   0    4                          Soybean   0      0      5   0    5   0    5   0    5                          Oat       0      0      5   0    5   0    5   0    5                          Sorghum   0      0      5   0    5   0    5   0    5                          Barley    0      0      5   0    5   0    5   0    5                          Cotton    0      0      5   0    5   0    5   0    5                          Sicklepod 0      0      5   0    5   0    5   0    5                          Barnyardgrass                                                                           0      0      5   0    5   0    5   0    4                          Foxtail   0      0      5   0    5   0    5   0    4                          ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                                    .sup.a Surviving plants expected to recover.                             

                  TABLE 12                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON PREEMERGENCE                                   PERFORMANCE OF 2-(1-CYANO-1-METHYLETHYL-                                      AMINO)-6-CYCLOPROPYLAMINO-4-METHOXY-5-                                        PYRIMIDINECARBONITRILE (Example XLIX)*                                               0.14                                                                          kg/   0.28 kg/ 0.56 kg/ 1.12 kg/                                                                             2.24 kg/                                       ha    ha       ha       ha     ha                                      CROP     K     V     K    V   K    V   K    V   K    V                        ______________________________________                                        Lima bean                                                                              0     5     0    5   0    5   0    4   100  0                        Corn     0     5     0    5   0    5   0    5   60   3                        Wild oat 0     5     0    5   0    5   30   4   75   4                        Sugarbeet                                                                              0     5     0    5   80   4   80   4   100  0                        Onion    30    4     100  0   100  0   100  0   100  0                        Green Fox-                                                                    tail     20    3     50   2   75   2   90   1   100  0                        Soybean  0     5     0    5   0    5   0    4   75   0                        Cotton   0     5     0    5   0    5   0    5   0    5                        Lettuce  --    --    --   --  90   2   100  0   100  0                        Mustard  --    --    --   --  90   2   100  0   100  0                        Sorghum  0     5     0    5   0    5   0    4   30   4                        Sicklepod                                                                              0     5     0    5   0    5   0    4   0    4                        Barley   0     5     0    5   0    5   0    5   0    4                        Barnyard-                                                                     grass    0     5     0    4   0    4   30   4   80   2                        Peanut   0     5     0    5   0    5   0    5   0    5                        Safflower                                                                              0     5     0    5   20   4   75   2   100  0                        Tomato   0     5     0    4   75   3   75   3   100  0                        Flax     0     5     0    5   75   4   75   3   100  0                        Rice     0     5     0    5   0    5   40   4   100  0                        Wheat    0     5     0    5   0    5   30   4   100  0                        Nutsedge 0     5     0    5   0    5   0    5   0    5                        ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                               

                  TABLE 13                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON PREEMERGENCE                                   PERFORMANCE OF 6-AMINO-2-(1-CYANO-1-METHYL-                                   ETHYLAMINO)-4-METHOXY-5-PYRIMIDINE-                                           CARBONITRILE (Example L)*                                                     0.56 kg/     1.12 kg/ 2.24 kg/ 4.48 kg/                                                                             8.96 kg/                                ha           ha       ha       ha     ha                                      CROP    K      V     K    V   K    V   K    V   K    V                        ______________________________________                                        Lima Bean                                                                             0      4     100  0   100  0   100  0   100  0                        Corn    0      5     60   4   100  0   100  0   100  0                        Wild Oat                                                                              0      5     10   4   100  0   100  0   100  0                        Lettuce 90     1     100  0   100  0   100  0   100  0                        Mustard 0      4     60   4   100  0   100  0   100  0                        Crabgrass                                                                             30     3     30   3   80   1   100  0   100  0                        Nutsedge                                                                              0      5     0    5   0    5   0    5   0    4                        ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                               

                  TABLE 14                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON PREEMERGENCE                                   PERFORMANCE OF 6-BUTYLAMINO-2-(1-CYANO-1-                                     METHYLETHYLAMINO)-4-METHOXY-5-PYRIMIDINE                                      CARBONITRILE (Ex. LI)*                                                                0.56 kg/                                                                             1.12 kg/  2.24 kg/  4.48 kg/                                           ha     ha        ha        ha                                         CROP      K.sup.a  K.sup.a   K     V   K     V                                ______________________________________                                        Lima Bean 0        0         0     5   0     4                                Corn      0        0         0     5   0     5                                Wild Oats 0        0         0     5   40    0                                Lettuce   0        0         75    0   100   0                                Mustard   0        40        100   0   100   0                                Crabgrass 0        10        40    3   100   0                                Nutsedge  0        0         0     5   0     5                                Morningglory                                                                            0        0         0     5   0     4                                Peanut    0        0         0     4   0     4                                Soybean   0        0         0     5   0     5                                Sicklepod 0        0         0     5   0     5                                Barley    0        0         0     5   0     5                                Wheat     0        0         0     5   0     4                                Flax      0        0         30    4   30    4                                Safflower 0        0         0     5   0     5                                Lambsquarter                                                                            30       75        100   0   100   0                                Barnyardgrass                                                                           0        0         0     5   0     5                                Green Foxtail                                                                           0        0         100   0   100   0                                Tomato    0        0         20    4   100   0                                ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                                    .sup.a Surviving plants expected to recover.                             

                  TABLE 15                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON PREEMERGENCE                                   PERFORMANCE OF 2-(1-CYANO-1-METHYL-                                           PROPYLAMINO)-6-CYCLOPROPYLAMINO-4-METHOXY-                                    5-PYRIMIDINECARBONITRILE (Example LII)*                                                                           4.48 kg/                                          0.56 kg/ha                                                                            1.12 kg/ha                                                                              2.24 kg/ha                                                                              ha                                        CROP      K       V     K     V   K     V   K    V                            ______________________________________                                        Lima Bean 0       5     0     5   100   0   100  0                            Corn      0       5     0     5   0     4    60  0                            Wild Oats 0       5     0     5   50    4   100  0                            Lettuce   0       4     75    2   100   0   100  0                            Mustard   100     0     100   0   100   0   100  0                            Crabgrass 25      3     60    2   75    1   100  0                            Tomato    0       4     100   0   100   0   100  0                            Wheat     0       5     0     4   100   0   100  0                            Safflower 0       5     0     5   20    4   100  0                            Peanut    0       5     0     4   0     4    0   4                            Soybean   0       5     0     5   0     4    80  2                            Cotton    0       5     0     5   0     5    0   5                            Rice      0       5     0     5   50    4    90  2                            Sorghum   0       5     0     5   0     4   100  0                            Barnyardgrass                                                                           0       5     0     3   100   0   100  0                            Sicklepod 0       5     0     5   0     5   100  0                            Morningglory                                                                            0       5     100   0   100   0   100  0                            Nutsedge  0       5     0     5   0     5    0   5                            ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                               

                  TABLE 16                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON PREEMERGENCE                                   PERFORMANCE OF 6-CYCLOPROPYLAMINO-2-                                          ISOPROPYLAMINO-4-METHOXY-5-PYRIMIDINE-                                        CARBONITRILE (Example LIV)*                                                   0.14 kg/     0.28 kg/ 0.56 kg/ 1.12 kg/                                                                             2.24 kg/                                ha           ha       ha       ha     ha                                      Crop    K      V     K    V   K    V   K    V   K    V                        ______________________________________                                        Lima Bean                                                                             0      5     0    5   0    5   0    4   75   2                        Corn    0      5     0    5   0    5   0    5   0    4                        Wild Oat                                                                              0      5     0    5   0    5   50   3   50   3                        Lettuce 0      4     0    4   100  0   100  0   100  0                        Mustard 0      4     0    4   75   4   90   2   100  0                        Crabgrass                                                                             0      5     0    3   75   3   90   1   100  0                        Tomato  0      5     0    5   50   3   100  0   100  0                        Safflower                                                                             0      5     0    5   0    5   0    5   0    4                        Flax    100    0     100  0   100  0   100  0   100  0                        Wheat   0      5     0    4   0    4   75   3   100  0                        Peanut  0      5     0    5   0    5   0    5   --   --                       Soybean 0      5     0    5   0    5   0    4   80   2                        Cotton  0      5     0    5   0    5   0    5   0    5                        Rice    0      5     0    5   0    5   0    4   20   4                        Sorghum 0      5     0    5   0    5   100  0   75   3                        Barnyard-                                                                     grass   0      5     0    5   80   2   100  0   100  0                        Sicklepod                                                                             0      5     0    5   0    5   0    5   20   4                        Morning-                                                                      glory   0      5     0    5   25   4   100  0   100  0                        Nutsedge                                                                              0      5     0    5   0    5   0    5   0    5                        ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                               

                  TABLE 17                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON PREEMERGENCE                                   PERFORMANCE OF 6-CYCLOPROPYLAMINO-2-DIETHYL-                                  AMINO-4-METHOXY-5-PYRIMIDINE-CARBONITRILE                                     (Example LV)*                                                                 1.12 kg/ha    2.24 kg/ha                                                                              4.48 kg/ha                                                                              8.96 kg/ha                                  Crop    K.sup.a   K       V   K     V   K     V                               ______________________________________                                        Lima Bean                                                                             0         0       5   0     5   0     4                               Corn    0         0       5   0     5   0     5                               Wild Oats                                                                             0         0       5   0     4   90    2                               Lettuce 0         0       4   100   0   100   0                               Mustard 0         0       4   90    1   100   0                               Crabgrass                                                                             0         100     0   100   0   100   0                               Nutsedge                                                                              0         0       5   0     5   0     5                               ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                                    .sup.a Surviving plants expected to recover.                             

                  TABLE 18                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON PREEMERGENCE                                   PERFORMANCE OF 2-CYCLOPROPYLAMINO-6-ISO-                                      PROPYLAMINO-4-METHOXY-5-PYRIMIDINE-                                           CARBONITRILE (Example LVIII)*                                                 2.24 kg/ha       4.48 kg/ha  8.96 kg/ha                                       Crop    K.sup.a      K       V     K     V                                    ______________________________________                                        Lima Bean                                                                             0            0       5     0     5                                    Corn    0            0       5     0     5                                    Wild Oats                                                                             0            0       5     0     5                                    Lettuce 0            75      2     75    2                                    Mustard 0            0       4     75    2                                    Crabgrass                                                                             0            100     0     100   0                                    Nutsedge                                                                              0            0       5     0     5                                    ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                                    .sup.a Surviving plants expected to recover.                             

                  TABLE 19                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON PREEMERGENCE                                   PERFORMANCE OF 2,6-BIS(CYCLOPROPYLAMINO)-4-                                   METHOXY-5-PYRIMIDINECARBONITRILE (Example LIX)*                               0.56 kg/ha    1.12 kg/ha                                                                              2.24 kg/ha                                                                              4.48 kg/ha                                  Crop    K.sup.a   K       V   K     V   K     V                               ______________________________________                                        Lima Bean                                                                             0         0       4   0     4   100   0                               Corn    0         0       5   0     5   30    2                               Wild Oats                                                                             0         25      4   25    4   100   0                               Lettuce 0         10      0   100   0   100   0                               Mustard 0         0       4   50    2   100   0                               Crabgrass                                                                             0         100     0   100   0   100   0                               Nutsedge                                                                              0         0       5   0     5   0     5                               ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                                    .sup.a Surviving plants expected to recover.                             

                  TABLE 20                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON PREEMERGENCE                                   PERFORMANCE OF 6-CYCLOPROPYLAMINO-4-                                          METHOXY-2-(1-METHYLPROPYLAMINO)-5-PYRIMIDINE-                                 CARBONITRILE (Example LX)*                                                            0.56 kg/ha                                                                              1.12 kg/ha  2.24 kg/ha                                      Crop      K.sup.a     K       V     K    V                                    ______________________________________                                        Lima Bean 0           0       5     0    4                                    Corn      0           0       5     0    5                                    Wild Oats 0           0       5     20   4                                    Lettuce   0           40      4     80   3                                    Mustard   0           100     0     95   2                                    Crabgrass 10          30      4     40   3                                    Soybean   0           0       5     0    5                                    Sorghum   0           0       5     0    5                                    Sesbania  0           0       5     60   4                                    Sicklepod 0           0       5     20   4                                    Green Foxtail                                                                           50          50      4     90   2                                    Peanuts   0           0       5     0    5                                    Cotton    0           0       5     0    5                                    Barnyardgrass                                                                           0           0       4     30   3                                    Johnsongrass                                                                            0           20      4     0    4                                    Downeybrome                                                                             10          10      4     20   4                                    Morningglory                                                                            0           0       5     0    5                                    ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                                    .sup.a Surviving plants expected to recover.                             

                  TABLE 21                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON PREEMERGENCE                                   PERFORMANCE OF 4-METHOXY-6-(1-METHYLETHYL-                                    AMINO)-2-(2-METHYLPROPYLAMINO)-5-PYRIMIDINE-                                  CARBONITRILE (Example LXI)*                                                             0.56 kg/ha   1.12 kg/ha                                                                              2.24 kg/ha                                   Crop      K.sup.a      K.sup.a   K.sup.a                                      ______________________________________                                        Lima Bean 0            0         0                                            Corn      0            0         0                                            Wild Oats 0            0         0                                            Lettuce   0            10        60                                           Mustard   0            0         50                                           Crabgrass 0            60        40                                           Soybean   O            O         O                                            Sorghum   0            0         0                                            Sesbania  0            0         50                                           Sicklepod 0            0         0                                            Green Foxtail                                                                           0            0         50                                           Peanuts   0            0         0                                            Cotton    0            0         0                                            Barnyardgrass                                                                           0            0         0                                            Johnsongrass                                                                            0            0         0                                            Downeybrome                                                                             0            0         0                                            Morningglory                                                                            0            0         0                                            ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                                    .sup.a Surviving plants expected to recover.                             

In the same way, the effect of the amount of active compound applied perhectare upon performance as a postemergence herbicide was determined forseveral of the herbicidal 5-pyrimidinecarbonitriles. The results appearin Tables 22-43.

                  TABLE 22                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON POST-                                          EMERGENCE PERFORMANCE OF 2-(1-CYANO-1-                                        METHYLPROPYLAMINO)-6-ISOPROPYLAMINO-4-                                        METHOXY-5-PYRIMIDINECARBONITRILE                                              (Example XXXIV)*                                                              0.28 kg/     0.56 kg/ 1.12 kg/ 2.24 kg/                                                                             4.48 kg/                                ha           ha       ha       ha     ha                                      Crop    K      V     K    V   K    V   K    V   K    V                        ______________________________________                                        Lima Bean                                                                             0      5     0    4   50   4   100  0   100  0                        Corn    0      5     0    5   0    5   0    5   0    4                        Wild Oats                                                                             0      5     0    5   0    4   10   4   30   4                        Lettuce 100    0     100  0   100  0   100  0   100  0                        Mustard 60     2     100  0   100  0   100  0   100  0                        Crabgrass                                                                             50     4     100  0   100  0   100  0   100  0                        ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                               

                  TABLE 23                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON POST-                                          EMERGENCE PERFORMANCE OF 2-(1-CYANO-1-                                        METHYLETHYLAMINO)-6-ISOPROPYLAMINO-4-                                         METHOXY-5-PYRIMIDINECARBONITRILE                                              (Example XXXV)*                                                                                                   2.24                                              0.28 kg/ha                                                                            0.56 kg/ha                                                                              1.12 kg/ha                                                                              kg/ha                                     Crop      K      V      K    V    K    V    K    V                            ______________________________________                                        Lima Bean 0      4      0    4    25   4    100  0                            Corn      0      5      0    5    30   4    60   3                            Wild Oat  0      5      0    5    0    5    50   4                            Sugarbeet 50     4      100  0    100  0    100  0                            Onion     80     2      100  0    100  0    100  0                            Green Foxtail                                                                           75     4      100  0    100  0    100  0                            Soybean   0      5      0    4    50   4    100  0                            Cotton    0      5      0    5    0    5    0    5                            Sorghum   0      5      0    5    0    4    0    4                            Sicklepod 0      4      0    4    0    4    50   4                            Barley    0      5      0    5    0    4    100  0                            Barnyardgrass                                                                           20     4      20   4    80   2    100  0                            Peanut    0      5      0    5    0    5    0    4                            Safflower 100    0      100  0    100  0    100  0                            Tomato    100    0      100  0    100  0    100  0                            Flax      0      4      80   3    100  0    100  0                            Rice      0      5      80   4    90   2    100  0                            Wheat     0      5      0    4    30   4    100  0                            Nutsedge  0      5      0    5    0    5    0    5                            Lettuce   --     --     100  0    100  0    --   --                           Mustard   --     --     100  0    100  0    --   --                           Crabgrass --     --     100  0    100  0    --   --                           ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                               

                  TABLE 24                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON POST-                                          EMERGENCE PERFORMANCE OF 2-(1-CYANO-1-                                        METHYLETHYLAMINO)-6-ETHYLAMINO-4-                                             METHOXY-5-PYRIMIDINECARBONITRILE                                              (Example XXXIII)*                                                             0.14         0.28     0.56     1.12   2.24                                    kg/ha        kg/ha    kg/ha    kg/ha  kg/ha                                   CROP    K      V     K    V   K    V   K    V   K    V                        ______________________________________                                        Lima Bean                                                                             0      5     0    5   0    5   75   4   100  0                        Corn    0      5     0    5   0    5   0    4   100  0                        Wild Oats                                                                             0      5     0    5   0    5   50   4   100  0                        Sugarbeet                                                                             75     3     100  0   100  0   100  0   100  0                        Onion   100    0     100  0   100  0   100  0   100  0                        Green   100    0     100  0   100  0   100  0   100  0                        Foxtail                                                                       Soybean 0      4     0    4   20   4   90   2   100  0                        Cotton  0      5     0    5   0    5   0    5   0    4                        Sorghum 0      5     0    5   0    5   0    5   0    4                        Sicklepod                                                                             0      4     0    4   50   4   75   4   100  0                        Barley  0      4     0    4   10   4   100  0   100  0                        Barnyard-                                                                             0      5     30   4   50   4   100  0   100  0                        grass                                                                         Peanut  0      5     0    5   0    5   100  0   100  0                        Safflower                                                                             60     4     75   3   100  0   100  0   100  0                        Tomato  75     4     100  0   100  0   100  0   100  0                        Flax    0      4     100  0   100  0   100  0   100  0                        Rice    10     4     20   4   80   2   100  0   100  0                        Wheat   0      5     0    5   0    5   75   4   100  0                        Nutsedge                                                                              0      5     0    5   0    5   0    5   0    5                        Lettuce --     --    100  0   100  0   100  0   100  0                        Mustard --     --    100  0   100  0   100  0   100  0                        Crabgrass                                                                             --     --    80   4   100  0   100  0   100  0                        ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                               

                  TABLE 25                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON POST-                                          EMERGENCE PERFORMANCE OF 6-ETHYLAMINO-2-                                      ISOPROPYLAMINO-4-METHOXY-5-PYRIMIDINE-                                        CARBONITRILE (Example XXXVI)*                                                 0.56         1.12     2.24     4.48   8.96                                    kg/ha        kg/ha    kg/ha    kg/ha  kg/ha                                   CROP    K      V     K    V   K    V   K    V   K    V                        ______________________________________                                        Lima Beans                                                                            0      4     0    4   0    4   0    4   0    3                        Corn    0      5     0    5   0    5   0    5   0    5                        Wild Oats                                                                             50     3     50   3   100  0   100  0   100  0                        Lettuce 100    0     100  0   100  0   100  0   100  0                        Mustard 100    0     100  0   100  0   100  0   100  0                        Crabgrass                                                                             50     3     50   4   90   3   100  0   100  0                        Nutsedge                                                                              0      5     0    5   0    5   0    5   0    5                        ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                               

                  TABLE 26                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON POST-                                          EMERGENCE PERFORMANCE OF 6-DIETHYLAMINO-2-                                    ISOPROPYLAMINO-4-METHOXY-5-PYRIMIDINE-                                        CARBONITRILE (Example XXXIX)*                                                        0.56 kg/ha                                                                             1.12 kg/ha                                                                              2.24 kg/ha                                                                              4.48 kg/ha                                Crop     K      V      K    V    K    V    K    V                             ______________________________________                                        Lima Beans                                                                             0      4      0    4    0    4    0    4                             Corn     0      4      0    4    0    4    0    4                             Wild Oats                                                                              95     1      100  0    100  0    100  0                             Lettuce  100    0      100  0    100  0    100  0                             Mustard  100    0      100  0    100  0    100  0                             Crabgrass                                                                              100    0      100  0    100  0    100  0                             Nutsedge 0      5      0    5    0    5    0    5                             ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                               

                  TABLE 27                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON POST-                                          EMERGENCE PERFORMANCE OF 2-ETHYLAMINO-6-                                      ISOPROPYLAMINO-4-METHOXY-5-PYRIMIDINE-                                        CARBONITRILE (Example XL)*                                                    0.56         1.12     2.24     4.48   8.96                                    kg/ha        kg/ha    kg/ha    kg/ha  kg/ha                                   Crop    K      V     K    V   K    V   K    V   K    V                        ______________________________________                                        Lima Beans                                                                            0      5     0    5   0    5   0    5   0    4                        Corn    0      5     0    5   0    5   0    5   0    5                        Wild Oats                                                                             0      5     0    5   0    5   0    5   0    4                        Lettuce 100    0     100  0   100  0   100  0   100  0                        Mustard 0      5     0    5   0    5   0    5   0    5                        Crabgrass                                                                             0      5     0    5   0    5   0    5   0    5                        Nutsedge                                                                              0      5     0    5   0    5   0    5   0    5                        ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                               

                  TABLE 28                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON POST-                                          EMERGENCE PERFORMANCE OF 6-ETHYLAMINO-4-                                      METHOXY-2-METHYLAMINO-5-PYRIMIDINE-                                           CARBONITRILE (Example XLII)*                                                           1.12 kg/ha                                                                            2.24 kg/ha  4.48 kg/ha                                       Crop       K.sup.a   K.sup.a     K     V                                      ______________________________________                                        Lima Beans 0         0           0     4                                      Corn       0         0           0     5                                      Wild Oats  0         0           0     4                                      Lettuce    0         60          100   0                                      Mustard    0         20          40    3                                      Crabgrass  0         0           20    4                                      Nutsedge   0         0           0     5                                      ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                                    .sup.a Surviving plants expected to recover.                             

                  TABLE 29                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON POST-                                          EMERGENCE PERFORMANCE OF 6-ISOPROPYL-                                         AMINO-4-METHOXY-2-METHYLAMINO-5-PYRIMIDINE-                                   CARBONITRILE (Example XLIII)*                                                         2.24 kg/ha                                                                             4.48 kg/ha  8.96 kg/ha                                       Crop      K.sup.a    K       V     K     V                                    ______________________________________                                        Lima Beans                                                                              0          0       4     0     4                                    Corn      0          0       5     0     5                                    Wild Oats 0          0       5     0     5                                    Lettuce   0          100     0     100   0                                    Mustard   0          100     0     100   0                                    Crabgrass 0          0       5     0     5                                    Nutsedge  0          0       5     0     5                                    ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                                    .sup.a Surviving plants expected to recover.                             

                  TABLE 30                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON POST-                                          EMERGENCE PERFORMANCE OF 6-DIETHYLAMINO-2-                                    ETHYLAMINO-4-METHOXY-5-PYRIMIDINE-                                            CARBONITRILE (Example XLV)*                                                          1.12 kg/ha                                                                            2.24 kg/ha                                                                              4.48 kg/ha                                                                              8.96 kg/ha                                 Crop     K.sup.a   K.sup.a   K     V   K     V                                ______________________________________                                        Lima Beans                                                                             0         0         0     4   0     4                                Corn     0         0         0     5   0     5                                Wild Oats                                                                              0         0         0     5   10    4                                Lettuce  0         60        100   0   100   0                                Mustard  0         30        80    2   90    1                                Crabgrass                                                                              0         20        75    2   80    2                                Nutsedge 0         0         0     5   0     5                                ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      of 5 signifying no chemical injury.                                           .sup.a Surviving plants expected to recover.                             

                  TABLE 31                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON POST-                                          EMERGENCE PERFORMANCE OF 4-ETHOXY-6-                                          DIETHYLAMINO-2-ISOPROPYLAMINO-5-PYRIMIDINE-                                   CARBONITRILE (Example XLVI)*                                                  0.28         0.56     1.12     2.24   4.48                                    kg/ha        kg/ha    kg/ha    kg/ha  kg/ha                                   CROP    K      V     K    V   K    V   K    V   K    V                        ______________________________________                                        Lima Bean                                                                             0      5     0    5   0    5   0    5   0    4                        Corn    0      5     0    5   0    5   0    5   0    5                        Wild Oats                                                                             0      5     0    5   0    5   0    5   0    4                        Lettuce 100    0     100  0   100  0   100  0   100  0                        Mustard 0      5     10   4   10   4   75   2   100  0                        Crabgrass                                                                             0      5     0    4   60   2   85   1   100  0                        Soybean 0      5     0    5   0    5   0    5   0    5                        Cotton  0      5     0    5   0    5   0    5   0    5                        Flax    0      5     0    4   20   4   100  0   100  0                        Peanut  0      5     0    5   0    5   0    5   0    5                        Rice    0      5     0    5   0    5   0    4   10   4                        Sugarbeet                                                                             --     --    --   --  0    4   20   3   0    3                        Rape    0      5     0    5   0    5   0    5   0    5                        Sorghum 0      5     0    5   0    5   0    5   0    5                        Barnyard-                                                                             0      5     0    5   0    5   0    5   0    5                        grass                                                                         Onion   0      4     0    4   10   3   100  0   100  0                        Safflower                                                                             0      5     0    5   0    5   0    5   0    5                        Prickly 0      5     0    5   0    5   0    4   0    4                        Sida                                                                          Morning-                                                                              0      5     0    5   0    5   20   4   90   2                        glory                                                                         Tomato  0      5     0    4   20   4   80   3   100  0                        Nutsedge                                                                              0      5     0    5   0    5   0    5   0    5                        ______________________________________                                         *Entries under K refer to percent kill; under V to plant vigor, a vigor o     5 signifying no chemical injury.                                         

                  TABLE 32                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON POST-                                          EMERGENCE PERFORMANCE OF 2-(1-CYANO-1-                                        METHYLETHYLAMINO)-4-METHOXY-6-(1-METHYL-                                      BUTYLAMINO)-5-PYRIMIDINECARBONITRILE                                          (Example XLVII)*                                                              0.28         0.56     1.12     2.24   4.48                                    kg/ha        kg/ha    kg/ha    kg/ha  kg/ha                                   CROP    K      V     K    V   K    V   K    V   K    V                        ______________________________________                                        Rice    0      5     0    5   0    5   0    5   0    5                        Flax    100    0     100  0   100  0   100  0   100  0                        Safflower                                                                             0      5     30   4   100  0   100  0   100  0                        Tomato  0      5     0    5   0    4   100  0   100  0                        Peanut  0      5     0    5   0    5   0    5   0    5                        Wheat   0      5     0    5   0    5   0    5   0    5                        Morning-                                                                              0      5     0    5   0    5   0    5   0    4                        glory                                                                         Sugarbeet                                                                             100    0     100  0   100  0   100  0   100  0                        Lima Bean                                                                             0      5     0    5   0    5   30   4   60   4                        Corn    0      5     0    5   0    5   0    5   0    5                        Soybean 0      5     0    5   0    5   0    5   0    5                        Oats    0      5     0    5   0    5   0    5   0    5                        Sorghum 0      5     0    5   0    5   0    5   0    5                        Barley  0      5     0    5   0    5   0    4   0    4                        Cotton  0      5     0    5   0    5   0    4   0    4                        Sicklepod                                                                             0      5     0    5   0    5   0    5   0    5                        Barnyard-                                                                             0      5     0    5   0    5   0    5   0    5                        grass                                                                         Foxtail 0      4     0    4   0    4   0    4   100  0                        ______________________________________                                         *Entries under K refer to percent kill; under V to plant vigor, a vigor o     5 signifying no chemical injury.                                         

                  TABLE 33                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON                                                POSTEMERGENCE PERFORMANCE OF 2-(1-CYANO-1-                                    METHYLETHYLAMINO)-6-(1-ISOPROPYL-2-                                           METHYLPROPYLAMINO)-4-METHOXY-5-PYRIMIDINE                                     CARBONITRILE (Example XLVIII)*                                                              4.48 kg/ha                                                                              8.96 kg/ha                                            Crop          K.sup.a   K.sup.a                                               ______________________________________                                        Lima Bean     0         0                                                     Corn          0         0                                                     Wild Oat      0         0                                                     Lettuce       0         60                                                    Mustard       0         0                                                     Crabgrass     0         0                                                     Nutsedge      0         0                                                     ______________________________________                                         *Entries under K refer to percent kill; under V to plant vigor, a vigor o     5 signifying no chemical injury.                                              .sup.a Surviving plants expected to recover.                             

                                      TABLE 34                                    __________________________________________________________________________    2-(1-CYANO-1-METHYLETHYLAMINO)-6-CYCLOPROPYLAMINO-4-                          METHOXY-5-PYRIMIDINECARBONITRILE (Example XLIX)*                                      0.14 kg/ha                                                                          0.28 kg/ha                                                                          0.56 kg/ha                                                                          1.12 kg/ha                                                                          2.24 kg/ha                                    Crop    K   V K   V K   V K   V K   V                                         __________________________________________________________________________    Lima Bean                                                                             0   5 0   4 80  2 100 0 100 0                                         Corn    0   5 0   5 0   4 100 0 100 0                                         Wild Oat                                                                              0   5 0   5 0   5 0   4 100 0                                         Sugarbeet                                                                             100 0 100 0 100 0 100 0 100 0                                         Onion   100 0 100 0 100 0 100 0 100 0                                         Green Foxtail                                                                         100 0 100 0 100 0 100 0 100 0                                         Soybean 0   5 0   5 0   4 100 0 100 0                                         Cotton  0   5 0   5 10  4 100 0 100 0                                         Sorghum 0   5 0   5 0   5 75  4 100 0                                         Sicklepod                                                                             0   4 30  4 50  4 100 0 100 0                                         Barnyardgrass                                                                         0   5 0   5 100 0 100 0 100 0                                         Peanut  0   5 0   5 0   4 100 0 80  2                                         Safflower                                                                             80  4 100 0 100 0 100 0 100 0                                         Tomato  100 0 100 0 100 0 100 0 100 0                                         Flax    75  4 100 0 100 0 100 0 100 0                                         Rice    10  4 100 0 100 0 100 0 100 0                                         Wheat   0   5 10  4 75  4 100 0 100 0                                         Nutsedge                                                                              0   5 0   5 0   4 0   4 0   4                                         Lettuce --  --                                                                              --  --                                                                              100 0 100 0 100 0                                         Mustard --  --                                                                              --  --                                                                              100 0 100 0 100 0                                         Crabgrass                                                                             --  --                                                                              --  --                                                                              100 0 100 0 100 0                                         __________________________________________________________________________     *Entries under K refer to percent kill; under V, to plant vigor, a vigor      rating of 5 signifying no chemical injury.                               

                                      TABLE 35                                    __________________________________________________________________________    EFFECT OF APPLICATION LEVEL ON POSTEMERGENCE PER-                             FORMANCE OF 6-AMINO-2-(1-CYANO-1-METHYLETHYLAMINO)-4-                         METHOXY-5-PYRIMIDINECARBONITRILE (Example L)*                                 0.56 kg/ha   1.12 kg/ha                                                                          2.24 kg/ha                                                                           4.48 kg/ha                                                                          8.96 kg/ha                                    Crop  K   V  K   V K   V  K   V K                                             __________________________________________________________________________    Lima Bean                                                                           30  4  75  3 100 0  100 0 100                                           Corn  0   5  0   5 0   4  0   4 100                                           Wild oat                                                                            0   5  10  4 50  3  100 0 100                                           Lettuce                                                                             100 0  100 0 100 0  100 0 100                                           Mustard                                                                             20  4  100 0 100 0  100 0 100                                           Crabgrass                                                                           0   5  0   5 0   4  100 0 100                                           Nutsedge                                                                            0   5  0   5 0   4  0   4 100                                           __________________________________________________________________________     *Entries under K refer to percent kill; under V, to plant vigor, a vigor      of 5 signifying no chemical injury.                                      

                                      TABLE 36                                    __________________________________________________________________________    EFFECT OF APPLICATION LEVEL ON POSTEMERGENCE PER-                             FORMANCE OF 6-BUTYLAMINO-2-(1-CYANO-1-METHYLETHY-                             LAMINO)-4-METHOXY-5-PYRIMIDINECARBONITRILE (Example LI)*                              0.28 kg/ha                                                                          0.56 kg/ha                                                                          1.12 kg/ha                                                                          2.24 kg/ha                                                                          4.48 kg/ha                                    Crop    K   V K   V K   V K   V K   V                                         __________________________________________________________________________    Lima Bean                                                                             0   4 0   4 50  3 100 0 100 0                                         Corn    0   5 0   5 0   5 0   5 0   5                                         Wild Oat                                                                              0   5 0   5 0   5 0   5 0   5                                         Lettuce 100 0 100 0 100 0 100 0 100 0                                         Mustard 0   5 0   4 75  3 100 0 100 0                                         Crabgrass                                                                             0   5 0   5 0   5 90  2 100 0                                         Nutsedge                                                                              0   5 0   5 0/ 5                                                                              0 5   0 5                                             Morningglory                                                                          0   5 0   4 20  4 100 0 100 0                                         Peanut  0   5 0   5 0   5 0   5 0   5                                         Soybean 0   5 0   5 0   5 0   5 60  2                                         Sicklepod                                                                             0   5 0   5 0   5 0   4 0   4                                         Barley  0   5 0   5 0   5 0   4 0   4                                         Wheat   0   5 0   5 0   5 0   5 0   4                                         Flax    0   5 0   5 75  4 100 0 100 0                                         Safflower                                                                             0   5 0   5 0   5 0   5 0   5                                         Lambsquarter                                                                          90  2 90  2 100 0 100 0 100 0                                         Barnyardgrass                                                                         0   5 0   5 0   5 0   5 0   5                                         Green Foxtail                                                                         0   4 30  4 100 0 100 0 100 0                                         Tomato  60  4 60  4 100 0 100 0 100 0                                         __________________________________________________________________________     *Entries under K refer to percent kill; under V, to plant vigor, a vigor      of 5 signifying no chemical injury.                                      

                  TABLE 37                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON                                                POSTEMERGENCE PERFORMANCE OF 2-(1-CYANO-1-                                    METHYLPROPYLAMINO)-6-CYCLOPROPYLAMINO-4-                                      METHOXY-5-PYRIMIDINECARBONITRILE (Example LII)*                                      0.56 kg/ha                                                                            1.12 kg/ha                                                                              2.24 kg/ha                                                                              4.48 kg/ha                                 Crop     K       V     K     V   K     V   K     V                            ______________________________________                                        Lima Bean                                                                              0       4     75    3   100   0   100   0                            Corn     0       5     0     5   0     5   0     5                            Wild Oat 0       5     0     5   0     5   50    4                            Lettuce  100     0     100   0   100   0   100   0                            Mustard  100     0     100   0   100   0   100   0                            Crabgrass                                                                              100     0     100   0   100   0   100   0                            Tomato   100     0     100   0   100   0   100   0                            Flax     90      1     100   0   100   0   100   0                            Wheat    0       5     0     5   20    4   100   0                            Safflower                                                                              100     0     100   0   100   0   100   0                            Peanut   0       5     0     5   0     5   0     5                            Soybean  0       5     20    4   100   0   100   0                            Cotton   0       4     25    4   100   0   100   0                            Rice     0       5     0     5   100   0   100   0                            Sorghum  0       5     0     5   100   0   100   0                            Sicklepod                                                                              20      4     20    4   75    4   90    2                            Barnyard-                                                                     grass    40      3     100   0   100   0   100   0                            Morningglory                                                                           25      4     100   0   100   0   100   0                            Nutsedge 0       5     0     5   0     5   50    4                            ______________________________________                                         *Entries under K refer to percent kill; under V, to plant vigor, a vigor      of 5 signifying no chemical injury.                                      

                                      TABLE 38                                    __________________________________________________________________________    EFFECT OF APPLICATION LEVEL ON POSTEMERGENCE PER-                             FORMANCE OF 6-CYCLOPROPYLAMINO-2-ISOPROPYLAMINO-4-                            METHOXY-5-PYRIMIDINECARBONITRILE (Example LIV)*                                       0.14 kg/ha                                                                          0.28 kg/ha                                                                          0.56 kg/ha                                                                          1.12 kg/ha                                                                          2.24 kg/ha                                    Crop    K   V K   V K   V K   V K   V                                         __________________________________________________________________________    Lima Bean                                                                             0   4 50  3 50  3 100 0 100 0                                         Corn    0   5 0   5 0   5 0   4 0   4                                         Wild Oat                                                                              0   5 0   4 100 0 100 0 100 0                                         Lettuce 100 0 100 0 100 0 100 0 100 0                                         Mustard 75  2 80  2 100 0 100 0 100 0                                         Crabgrass                                                                             50  4 50  4 100 0 100 0 100 0                                         Tomato  100 0 100 0 100 0 100 0 100 0                                         Safflower                                                                             100 0 100 0 100 0 100 0 100 0                                         Flax    100 0 100 0 100 0 100 0 100 0                                         Wheat   10  4 20  4 50  4 100 0 100 0                                         Peanut  0   5 0   5 0   5 0   5 0   5                                         Soybean 0   4 25  4 25  4 100 0 100 0                                         Cotton  0   5 0   5 0   4 50  4 90  2                                         Rice    0   5 0   4 25  4 100 0 100 0                                         Sorghum 0   5 0   5 0   4 100 0 100 0                                         Barnyardgrass                                                                         0   4 50  3 100 0 100 0 100 0                                         Sicklepod                                                                             0   4 75  3 100 0 100 0 100 0                                         Morningglory                                                                          0   4 0   4 100 0 100 0 100 0                                         Nutsedge                                                                              0   5 0   5 0   5 0   5 0   5                                         __________________________________________________________________________     *Entries under K refer to percent kill; under V, to plant vigor, a vigor      of 5 signifying no chemical injury.                                      

                                      TABLE 39                                    __________________________________________________________________________    EFFECT OF APPLICATION LEVEL ON POSTEMERGENCE PER-                             FORMANCE OF 6-CYCLOPROPYLAMINO-2-DIETHYLAMINO-4-                              METHOXY-5-PYRIMIDINECARBONITRILE (Example LV)*                                0.56 kg/ha   1.12 kg/ha                                                                          2.24 kg/ha                                                                           4.48 kg/ha                                                                          8.96 kg/ha                                    Crop  K   V  K   V K   V  K   V K   V                                         __________________________________________________________________________    Lima Bean                                                                           0   5  0   5 0   5  0   4 0   3                                         Corn  0   5  0   5 0   5  0   5 0   5                                         Wild Oats                                                                           100 0  100 0 100 0  100 0 100 0                                         Lettuce                                                                             100 0  100 0 100 0  100 0 100 0                                         Mustard                                                                             75  4  100 0 100 0  100 0 100 0                                         Crabgrass                                                                           25  4  50  4 100 0  100 0 100 0                                         Nutsedge                                                                            0   5  0   5 0   5  0   5 0   5                                         __________________________________________________________________________     *Entries under K refer to percent kill; under V to plant vigor, a vigor o     5 signifying no chemical injury.                                         

                                      TABLE 40                                    __________________________________________________________________________    EFFECT OF APPLICATION LEVEL ON POSTEMERGENCE PER-                             FORMANCE OF 2-CYCLOPROPYLAMINO-6-ISOPROPYLAMINO-4-                            METHOXY-5-PYRIMIDINECARBONITRILE (Example LVIII)*                             0.56 kg/ha   1.12 kg/ha                                                                          2.24 kg/ha                                                                           4.48 kg/ha                                                                          8.96 kg/ha                                    Crop  K   V  K   V K   V  K   V K   V                                         __________________________________________________________________________    Lima Bean                                                                           0   4  0   4 0   4  0   4 0   4                                         Corn  0   5  0   5 0   5  0   5 0   5                                         Wild Oats                                                                           0   5  0   5 0   5  0   5 20  4                                         Lettuce                                                                             100 0  100 0 100 0  100 0 100 0                                         Mustard                                                                             75  2  75  2 75  2  90  1 100 0                                         Crabgrass                                                                           0   5  0   4 0   3  0   3 0   3                                         Nutsedge                                                                            0   5  0   5 0   5  0   5 0   5                                         __________________________________________________________________________     *Entries under K refer to percent kill; under V to plant vigor, a vigor o     5 signifying no chemical injury.                                         

                  TABLE 41                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON                                                POSTEMERGENCE PERFORMANCE OF 2,6-BIS                                          (CYCLOPROPYLAMINO)-4-METHOXY-5-PYRIMIDINE-                                    CARBONITRILE (Example LIX)*                                                          0.56 kg/ha                                                                              1.12 kg/ha  2.24 kg/ha                                       Crop     K       V       K     V     K     V                                  ______________________________________                                        Lima Bean                                                                              100     0       100   0     100   0                                  Corn     0       5       0     5     0     4                                  Wild Oats                                                                              0       4       50    3     100   0                                  Lettuce  100     0       100   0     100   0                                  Mustard  75      3       100   0     100   0                                  Crabgrass                                                                              0       4       100   0     100   0                                  Nutsedge 0       5       0     5     0     5                                  ______________________________________                                         *Entries under K refer to percent kill; under V to plant vigor, a vigor o     5 signifying no chemical injury.                                         

                                      TABLE 42                                    __________________________________________________________________________    EFFECT OF APPLICATION LEVEL ON POSTEMERGENCE PER-                             FORMANCE OF 6-CYCLOPROPYLAMINO-4-METHOXY-2-(1-                                METHYLPROPYLAMINO)-5-PYRIMIDINECARBONITRILE                                   (Example LX)*                                                                         0.14 kg/ha                                                                          0.28 kg/ha                                                                          0.56 kg/ha                                                                          1.12 kg/ha                                                                          2.24 kg/ha                                    Crop    K   V K   V K   V K   V K   V                                         __________________________________________________________________________    Lima Bean                                                                             60  3 60  3 80  2 80  2 100 0                                         Corn    0   5 0   5 0   5 0   4 0   4                                         Wild Oats                                                                             0   4 20  3 80  2 70  2 90  2                                         Lettuce 100 0 100 0 100 0 100 0 100 0                                         Mustard 60  3 80  3 100 0 100 0 100 0                                         Crabgrass                                                                             20  4 60  4 60  2 70  2 100 0                                         Soybean 0   4 50  3 30  3 80  3 80  3                                         Sorghum 0   3 0   3 20  3 20  3 70  3                                         Sesbania                                                                              100 0 100 0 100 0 100 0 100 0                                         Sicklepod                                                                             60  3 100 0 100 0 100 0 100 0                                         Green Foxtail                                                                         100 0 70  3 100 0 100 0 100 0                                         Peanuts 0   4 0   4 0   3 0   3 100 0                                         Cotton  70  3 80  3 80  3 100 0 100 0                                         Barnyardgrass                                                                         0   3 60  3 60  3 100 0 100 0                                         Johnsongrass                                                                          40  4 50  4 70  3 70  3 95  2                                         Downeybrome                                                                           0   4 95  3 90  3 100 0 100 0                                         Morningglory                                                                          0   4 0   4 0   3 100 0 100 0                                         __________________________________________________________________________     *Entries under K refer to percent kill; under V to plant vigor, a vigor o     5 signifying no chemical injury.                                         

                  TABLE 43                                                        ______________________________________                                        EFFECT OF APPLICATION LEVEL ON                                                POSTEMERGENCE PERFORMANCE OF 4-METHOXY-6-                                     (1-METHYLETHYLAMINO)-2-(2-METHYLPROPY-                                        LAMINO)-5-PYRIMIDINECARBONITRILE (Example LXI)*                                        0.14 kg/ha                                                                             0.28 kg/ha 0.56 kg/ha                                       Crop       K      V       K     V    K     V                                  ______________________________________                                        Lima Bean  0      4       0     3    0     3                                  Corn       0      5       0     5    0     5                                  Wild Oats  0      4       0     4    20    3                                  Lettuce    0      4       20    4    100   0                                  Mustard    0      4       0     4    30    3                                  Crabgrass  20     3       30    3    70    3                                  Soybean    0      5       0     4    0     3                                  Sorghum    0      5       0     5    0     4                                  Sesbania   95     2       100   0    100   0                                  Sicklepod  0      4       30    3    30    3                                  Green Foxtail                                                                            95     3       95    2    90    3                                  Peanuts    0      4       0     4    0     4                                  Cotton     0      5       0     4    0     5                                  Barnyardgrass                                                                            0      5       0     4    0     3                                  Johnsongrass                                                                             0      5       0     4    20    4                                  Downeybrome                                                                              0      4       0     4    30    3                                  Morningglory                                                                             0      5       0     5    0     5                                  ______________________________________                                         *Entries under K refer to percent kill; under V to plant vigor, a vigor o     5 signifying no chemical injury.                                         

The following herbicidal 5-pyrimidinecarbonitriles are prepared by themethods described above. In general, although these compounds exhibitherbicidal activity, a number of them are not as effective as thepreferred active compounds:6-amino-2-ethylamino-4-methoxy-5-pyrimidinecarbontrile,2-(1-cyano-1-methylethylamino)-4-methoxy-6-propylamino-5-pyrimidinecarbonitrile,6-cyclopropylamino-2-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile,2-diethylamino-4-methoxy-6-methylamino-5-pyrimidinecarbonitrile,2-diethylamino-6-dimethylamino-4-methoxy-5-pyrimidinecarbonitrile,2-ethylamino-4-methoxy-6-propylamino-5-pyrimidinecarbonitrile,2-diethylamino-4-methoxy-6-propylamino-5-pyrimidinecarbonitrile,2-ethylamino-4-methoxy-6-methylamino-5-pyrimidinecarbonitrile,6-dimethylamino-2-ethylamino-4-methoxy-5-pyrimidinecarbonitrile,6-isopropylamino-4-methoxy-2-(1-methylpropylamino)-5-pyrimidinecarbonitrile,2-isopropylamino-4-methoxy-6-(1-methylpropylamino)-5-pyrimidinecarbonitrile,2-isopropylamino-4-methoxy-6-propylamino-5-pyrimidinecarbonitrile,2-isopropylamino-4-methoxy-6-(2-methylpropylamino)-5-pyrimidinecarbonitrile,6-ethylamino-4-methoxy-2-methylethylamino-5-pyrimidinecarbonitrile,4-ethoxy-6-ethylamino-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile,6-ethylamino-4-methoxy-2-(2-methylpropylamino)-5-pyrimidinecarbonitrile,2-(1-cyano-1-methylpropylamino)-4-ethoxy-6-isopropylamino-5-pyrimidinecarbonitrile,2,6-diethylamino-4-isopropoxy-5-pyrimidinecarbonitrile,6-ethylamino-4-methoxy-2-(1-methylpropylamino)-5-pyrimidinecarbonitrile,2-amino-6-ethylamino-4-methoxy-5-pyrimidinecarbonitrile,2-amino-6-cyclopropylamino-4-methoxy-5-pyrimidinecarbonitrile, and2-amino-6-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile.

The active 5-pyrimidinecarbonitriles of this invention may be utilizedin diverse formulations to produce the herbicidal compositionscontemplated herein. The herbicidal compositions contain between about0.5% and 95% active 5-pyrimidinecarbonitrile, together with betweenabout 4% and 98.5% agriculturally acceptable carrier, and between about1% and 15% surfactant, by weight. As is well known in the art, theformulation and mode of application of an herbicidal composition mayaffect its activity in a given application. Thus, the herbicidal5-pyrimidinecarbonitriles disclosed herein may be formulated intogranules, wettable powders, emulsifiable concentrates, solutions, orother known forms, depending on the mode of application.

Granular formulations are particularly useful for aerial application.These formulations may be of several types. Large particles of anabsorbent carrier such as attapulgite or kaolin clay, corncobs, expandedmica, and so forth, may be impregnated with solutions of the activecompounds. The active 5-pyrimidinecarbonitriles in solution or as aslurry may also be sprayed onto the surface of the absorbent particles.The core of the particle may be watersoluble or insoluble. Aparticularly useful type of particle is one in which a wettable powderis applied as a surface coating to an insoluble granule such that thewettable powder may be dispersed on contact with moisture. Granules maybe produced by compacting dusts or powders, by extrusion through a die,or by use of a granulating disk. Granular formulations may vary widelyin concentration, containing as little as 0.5% or as much as about 20%active compound.

Wettable powders in the form of finely divided particls, which dispersereadily in water or other dispersants, are useful formulations for bothpreemergence and postemergence herbicides. A wettable powder typicallycontains a carrier such as a readily wetted inorganic diluent; forexample, Fuller's earth, kaolin clays or silicas mixed with about 5% to80%, but preferably at least 50%, herbicidally active compound andlesser amounts of surfactants.

Emulsifiable concentrates, which are homogeneous liquid or pastecompositions dispersible in water or other dispersants, may consistentirely of the active 5-pyrimidinecarbonitriles of this inventiontogether with a liquid or solid surfactant. They may also containagriculturally acceptable liquid carriers such as xylene, naptha,isophorone or other organic solvents.

Typical surfactants used in agricultural formulations include, forexample, the alkyl and aralkyl sulfonates and sulfates and their sodiumsalts, polyethylene oxides, sulfonated oils, fatty acid esters ofpolyhydric alcohols, and other types of surface active agents, many ofwhich are available in commerce. Surfactants, when used, normallycomprise from about 1% to 15% by weight of the herbicidal composition.

The herbicidal compositions of this invention may be applied withoutfurther dilution or as dilute solutions, emulsions, or suspensions inwater or other suitable diluents. The herbicidal compositions may beapplied to the area wherein control is desired by spraying thecompositions onto the undesired vegetation or the surface of the soil ifthey are liquids, or by distribution from mechanical equipment in thecase of solids. The surface-applied material may also be blended intothe upper layer of soil by cultivation, or left as applied in order togain the optimum results.

The herbically active compounds of this invention may be formulated andapplied together with insecticides, fungicides, nematicides, fertilizersand other agricultural chemicals. In formulating and applying theherbicidal compositions of this invention, either alone or with otheragricultural chemicals, herbicidally effective amounts of the activecompounds are employed. The amount constituting an effective amount isvariable, but generally, a uniform application of between about 0.1 and9 kilograms per hectare is effective, for example, 0.28 to 4.48kilograms per hectare.

It will be apparent to those skilled in the art that variousmodifications may be made in the formulation of the herbicidalcompositions of this invention, and in their application, withoutdeparting from the scope and spirit of this invention as defined in thefollowing claims:

I claim: .[.1. A chemical compound having the structural formula##STR3## wherein amino..]. .[.2. A chemical compound of claim 1 whereinthe halogen is chlorine..].
 3. A chemical compound having the structuralformula ##STR4## wherein (a) R² is a radical selected from amino, loweralkylamino, lower cycloalkylamino, di(lower alkyl)amino, and[alpha-cyano(lower alkyl)]amino;(b) R⁴ is a lower alkoxy radical; and(c) R⁶ is a radical selected from amino, lower alkylamino, lowercycloalkylamino, and di(lower alkyl)amino;with the proviso that neitherR² nor R⁶ is tert-butylamino; and provided further that when R² isisopropylamino, R⁶ is other than n-butylamino; and when R² ismethylethylamino, R⁶ is other than isopropylamino; and when R² isdiethylamino, R⁶ is other than amino.
 4. A chemical compound of claim 3wherein R² is selected from lower alkylamino (except tert-butylamino)and [alpha-cyano-(lower alkyl)]amino; and R⁶ is selected from loweralkylamino (except tert-butylamino) and lower cycloalkylamino.
 5. Achemical compound of claim 4 wherein R² is selected from ethylamino,isopropylamino, 1-methylpropylamino, 2-methylpropylamino, and1-cyano-1-methylethylamino; R⁴ is methoxy or ethoxy; and R⁶ is selectedfrom ethylamino, isopropylamino and cyclopropylamino.
 6. The chemicalcompound of claim 5 which is2-(1-cyano-1-methylethylamino)-6-ethylamino-4-methoxy-5-pyrimidinecarbonitrile.
 7. The chemical compound of claim 5 which is2-(1-cyano-1-methylethylamino)-6-cyclopropyl-amino-4-methoxy-5-pyrimidinecarbonitrile.
 8. The chemical compound of claim 5 which is2-(1-cyano-1-methylethylamino)-6-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile.
 9. An herbicidal composition comprising an herbicidallyeffective amount of at least one of the chemical compounds of claim 3 inadmixture with an agriculturally acceptable carrier and a surfactant.10. An herbicidal composition of claim 9 wherein R² is selected fromlower alkylamino (except tert-butylamino) and [alpha-cyano(loweralkyl)]amino; and R⁶ is selected from lower alkylamino (excepttert-butylamino) and lower cycloalkylamino.
 11. An herbicidalcomposition of claim 10 wherein R² is selected from ethylamino,isopropylamino, 1-methylpropylamino, 2-methylpropylamino, and1-cyano-1-methylethylamino; R⁴ is methoxy or ethoxy; and R⁶ is selectedfrom ethylamino, isopropylamino and cyclopropylamino.
 12. An herbicidalcomposition of claim 11 in which the chemical compound is2-(1-cyano-1-methylethylamino)-6-ethylamino-4-methoxy-5-pyrimidinecarbonitrile.
 13. An herbicidal composition of claim 11 in which the chemicalcompound is2-(1-cyano-1-methylethylamino)-6-cyclopropylamino-4-methoxy-5-pyrimidinecarbonitrile.
 14. An herbicidal composition of claim 11 in which thechemical compound is2-(1-cyano-1-methylethylamino)-6-isopropylamino-4-methoxy-5-pyrimidinecarbontrile.
 15. A method of controlling plant growth which comprisesapplying to the locus of the plants an herbicidally effective amount ofa chemical compound of claim
 3. 16. A method of claim 15 wherein thechemical compound is selected from2-(1-cyano-1-methylethylamino)-6-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile,2-(1-cyano-1-methylethylamino)-6-ethylamino-4-methoxy-5-pyrimidinecarbonitrile,and2-(1-cyano-1-methylethylamino)-6-cyclopropylamino-4-methoxy-5-pyrimidinecarbonitrile.
 17. A method of claim 16 wherein the growth of weeds iscontrolled without substantially affecting Zea mays in the same locus. Amethod of claim 16 wherein the growth of weeds is controlled withoutsubstantially affecting Gossypium hirsutum in the same locus.
 19. Themethod of claim 18 wherein the chemical compound is2-(1-cyano-1-methylethylamino)-6-isopropylamino-4-methoxy-5-pyrimidinecarbonitrile.
 20. A method of claim 16 wherein the growth of weeds iscontrolled without substantially affecting Sorghum vulgare in the samelocus.
 21. A method of claim 16 wherein the growth of weeds iscontrolled without substantially affecting Glycine max in the samelocus.
 22. A method of claim 16 wherein the growth of weeds iscontrolled without substantially affecting Arachis hypogaea in the samelocus.